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Published online: 23rd May, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14070
Thymidine, 2-Thiothymidine, and 2-Selenothymidine: Comparison of Mismatch Discriminations

Takaki Habuchi, Takao Yamaguchi, and Satoshi Obika

*,

Abstract

Oligonucleotides modified using 2-thiothymidine (S2T) or 2-selenothymidine (Se2T), which are thymidine analogs bearing either sulfur or selenium atoms, respectively, have been independently shown to suppress the formation of mismatched wobble base pairs with guanine when forming a duplex with single stranded DNA. However, limited data comparing the base discriminations of S2T- and Se2T-modified oligonucleotides, especially toward single stranded RNA, are available. Here, we report a comprehensive data set of the base discriminations of S2T- and Se2T-modified oligonucleotides toward both single stranded DNA and RNA. Our results demonstrate that S2T- and Se2T-modified oligonucleotides have similar base discrimination abilities. An important feature observed in both the S2T- and Se2T-modified oligonucleotides is their extremely high base discrimination toward single stranded RNA. Thus, S2T and Se2T modifications may be useful for therapeutic oligonucleotides targeting single stranded RNAs.

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Published online: 23rd May, 2019

Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14086
Uncariagambiriines B and C, Alkaloid-catechin Hybrids from Uncaria gambir Leaves

Mutsumi Oshima, Hiroe Aoyama, Yuuki Shimozu, Shoko Taniguchi, Takanori Miura, and Tsutomu Hatano*

*Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Okayama 700-8530, Japan

Abstract

Gambiers, aqueous extracts from the leaves and twigs of Uncaria gambir, are used medicinally in Asian countries. Previously, we reported the isolation of uncariagambiriine (1) from U. gambir leaves, and its unique structure regarded as a catechin-alkaloid hybrid. Our continuing studies led to the isolation of two previously undescribed compounds named uncariagambiriines B (2) and C (3), in addition to the flavonoid glycosides, hyperoside and isoquercitrin. The structures of 2 and 3, isomeric to 1, were elucidated based on their spectral data.

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Published online: 22nd May, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14087
An Efficient Three-Component Synthesis of Novel Spiro[Pyrazole-4,2’-Quinazoline] Derivatives

Hayate Nagabuchi, Eiichi Masumoto, Fumi Okabe-Nakahara, and Hiroshi Maruoka*

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan

Abstract

A simple, efficient, and three-component procedure has been developed for the synthesis of a series of spiropyrazol-3-one derivatives containing dihydroquinazoline moiety by the reaction of 1H-pyrazole-4,5-diones, 2-aminobenzophenones, and ammonium acetate in moderate to good yields. This method provides several advantages such as operational simplicity, shorter reaction time, and higher yields. All the synthesized compounds were characterized by spectroscopic analysis.

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Published online: 21st May, 2019

Review | Regular issue | Prepress
DOI: 10.3987/REV-19-905
The Synthetic Methods of 1,3,2-Diazaphosphinine Systems

Tarik E. Ali,* Mohammed A. Assiri, Ahmed M. Fouda, Mohamed M. Hassan, and Noha M. Hassanin

*Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo 11711, Egypt

Abstract

The present review considers all the literature data on methods developed for the synthesis of 1,3,2-diazaphosphinine systems starting from their appearance up to end 2018. The described main methods depended on the cyclization of 1,3-diamines, 1,2-aminoamide (β-aminoamide) and 1,2-aminonitrile (β-aminonitrile) compounds with phosphorus halides and sulfides.

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Published online: 21st May, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14085
A Mild and Efficient Ga(OTf)3-Catalysed Friedländer Reaction for the Synthesis of Quinolines

Hani Mutlak A. Hassan* and Iuliana Denetiu

*King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589 80216, Saudi Arabia

Abstract

The application of gallium triflate [Ga(OTf)3] for the synthesis of quinolines via the Friedländer reaction is described. This mild and straightforward method employed only 1 mol% of Ga(OTf)3 to deliver the quinoline products in excellent yields, demonstrating the high catalytic activity of this rare earth metal triflate.

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Published online: 13th May, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14075
Synthesis of Steroidal [1,2,4]triazolo[1,5-a]pyrimidines and their Antiproliferative Activities

Ning-Juan Fan, Jiang-Jiang Tang, Yuan-Feng Li, Yu-Bin Bai, and Xiao-Min Zhao*

*College of Veterinary Medicine, Northwest A&F University, Yangling, Shaanxi 712100, China

Abstract

A facile strategy for the synthesis of steroidal [1,2,4]triazolo[1,5-a]pyrimidines 5a-g and 6a-g has been accomplished via a one-pot reaction of steroidal ketones, aromatic aldehydes and 3-amino-1,2,4-triazole in the presence of potassium tert-butoxide in refluxing tert-butanol. All the synthesized heterosteroids were evaluated for in vitro antiproliferative activity against human cancer cells by sulforhodamine B (SRB) assays. The preliminary results showed that compounds 6a and 6e possessed potent antiproliferative activities.

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Published online: 7th May, 2019

Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14067
Design, Synthesis and Insecticidal Activity of 1-Methyl-3-(5-aryl-4,5-dihydroisoxazol-3-yl)-1H-pyrazole-5-carboxamides

Liangkun Zhong, Fan Zhang, Tao Jiang, Xinghai Liu, Tianming Xu, Chengrong Ding, Jie Chen, Jing Yuan,* and Chengxia Tan*

*College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China

Abstract

Pyrazole and its derivatives are a kind of important heterocyclic compounds used in agrochemicals development. In this research, a series of novel 1-methyl-3-(5-aryl-4,5-dihydroisoxazol-3-yl)-1H-pyrazole-5-carboxamides were synthesized and confirmed by 1H NMR, 13C NMR and ESI-MS. The preliminary bioactivity indicated that most title compounds showed excellent potency against Mythimna separate (Walker) at 500 mg/L, compounds ZJ4, ZJ12, ZJ16, ZJ17 showed moderate insecticidal activity against Aphis craccivora at 500 mg/L. Especially, compounds ZJ4, ZJ12, ZJ17 exhibited around 60% insecticidal activities against M. separate at 100 mg/L. The results indicated that the potential of these pyrazole-5-carboxamides containing arylisoxazoline fragment to be utilized in pesticide discovery through further development.

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Published online: 26th April, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14073
Isobenzofuranone Derivatives from the Roots of Phlomis betonicoides and Their Bioactivity

Mu-Yao Li, Ling-Min Liao, Qi-Yan Sun, Miao Dong, Min Zhou, Yan-Qing Ye, Yi-Jian Chen, Qiu-Fen Hu, and Wei-Guang Wang

*Key Laboratory of Chemistry in Ethnic Medicinal Resources, Yunnan Minzu University, Kunming 650031, China

Abstract

Three new (1-3) together with three known (4-6) isobenzofuranone derivatives, were isolated from the roots of Phlomis betonicoides. Their structures were elucidated by spectroscopic methods, including extensive 1D- and 2D-NMR techniques. Compounds 1-6 were evaluated for their anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) activity. The results showed that compounds 1-6 showed weak inhibition with diameter of inhibition zone of (IZD) of 9.2±1.2, 8.6±1.5, 9.8±1.6, 11.4±1.2, 8.2±1.0 and, 11.6±1.3 mm, respectively. Compounds 1-6 were also tested for the antioxidant activity, and they showed good antioxidant activity with an IC50 value of 4.6±0.8, 4.4±0.6, 4.0±0.6, 4.2±0.7, 4.8±0.6, and 4.1±0.5 μg/mL, respectively.

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Published online: 26th April, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14078
Ultrafast and Diastereoselective Synthesis of 3-Spirocyclopropyl-2-oxindoles Bearing Three Continuous All-Carbon Quaternary Centers

Aixin Geng, Hao Cui, Liyuan Zhang, Tao Lu,* and Yong Zhu*

*Department of Organic Chemistry, School of Science, China Pharmaceutical University, 639 Longmian Avenue, Nanjing 211198, China

Abstract

Synthesis of 3-spirocyclopropyl-2-oxindoles bearing three continuous all-carbon quaternary centers by the domino Michael-alkylation reaction between 3-chlorooxindole and isatylidenemalononitrile is described. Remarkably, the reaction proceeded in exceptionally high efficiency (up to 99% yield within 2 min) and excellent diastereoselectivity (>25:1 dr for all the examples).

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Published online: 25th April, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14059
Practical Synthesis of Pimobendan

Ping Zou, Lin Hu, Xi-Meng Yan, Xiao-Yue Li, Wanguo Wei, Xiao-Long Qiu,* and Shao-Hua Gou*

*Wisdom Pharmaceutical Co. Ltd., No. 18, Qinghua Road, Haimen, Jiangsu, 226123, China

Abstract

Pimobendan is a calcium sensitizer and a selective inhibitor of phosphodiesterase III (PDE3) with positive inotropic and vasodilator effects. Several attempts have been made to synthesize this drug. In this work, a facile synthetic route for the preparation of pimobendan from readily available starting materials and easily handled reagents is provided.

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Published online: 25th April, 2019

Review | Regular issue | Prepress
DOI: 10.3987/REV-19-908
Recent Application of ortho-Quinodimethane Chemistry for Synthesis of Heterocyclic Compounds

Yuji Matsuya*

*Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan

Abstract

The o-quinodimethanes, generated by concerted 4π-electrocyclic ring-opening of benzocyclobutenes, have been widely utilized as a powerful intermediate for the construction of various fused-cyclic frameworks. In this review, recent applications for the construction of heterocycles as well as their biological aspects are surveyed.

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Published online: 23rd April, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14046
Catalyst-Free Tandem Reaction for the Synthesis of Tetrahydro-1,2,3-triazine Derivatives

Kewei Wang, Huijun Liu, Yong Guo, Gang Yi,* Zhifang Jia,* and Feng Feng

*Department of Chemistry and Chemical Engineering, Shanxi Datong University, Datong, 037009, China

Abstract

A simple and efficient method for the synthesis of tetrahydro-1,2,3-triazine derivatives was developed through a one-pot ring-opening/ring-closing tandem reaction. By the tandem reaction, various previously unreported tetrahydro-1,2,3-triazines were prepared by cyclopropane derivatives and NaN3 with 90–97% yields under the catalyst-free conditions.

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Published online: 23rd April, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14062
Reaction of 2-Imino-2H-chromene-3-carboxamide with Phosphorus Halides: Synthesis of Some Novel Chromeno[2,3-d][1,3,2]diazaphosphinines and Chromeno[4,3-c][1,2]azaphosphole and Their Antioxidant and Cytotoxicity Properties

Tarik E. Ali,* Mohammed A. Assiri, Hafez M. El-Shaaer, Ahmed M. Fouda, Mohamed M. Hassan, and Noha M. Hassanin

*Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo, Egypt

Abstract

Novel 1,2-azaphosphole and 1,3,2-diazaphosphinines containing a chromene ring have been obtained from the treatment of 2-imino-2H-chromene-3-carboxamide (1) with some phosphorus halides. The compounds were evaluated for antioxidant and cytotoxic activities. Among the synthesized compounds, compound 4 exhibited the most potent antioxidant agents in comparison with ascorbic acid as standard antioxidant. Also, compound 4 recorded potentially cytotoxicity against all four cell lines.

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Published online: 22nd April, 2019

Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14071
Facile Sodium Metabisulfite Mediated Synthesis of 1,2-Disubstituted Benzimidazoles and Cytotoxicity Evaluation

Bui Thi Buu Hue,* Hien Minh Nguyen, Mai Van Hieu, Danh La Duc Thanh, Nguyen Hoang Son, Tran Quang De, and Hiroyuki Morita*

*Department of Chemistry, College of Natural Sciences, Can Tho University, Viet Nam

Abstract

A library of twenty-four, structurally diverse, 2-substituted and 1,2-disubstituted benzimidazole derivatives (4a-x) was designed and synthesized. The benzimidazole derivatives were constructed by a one-pot condensation reaction between 1,2-phenylenediamines and aromatic aldehydes under mild oxidation conditions utilizing inexpensive and non-toxic inorganic salt sodium metabisulfite. These compounds were assayed for cytotoxicities against five cancer cell lines; cervical (HeLa), breast cancer (MCF7), lung cancer (A549), stomach cancer (GSU) and Kato III cell lines in vitro. Most of the compounds had slightly inhibitory effects against all or limited tested cell lines. Among them, compound 4q showed moderate cytotoxicity against HeLa, MCF-7, A549, and Kato III cell lines with IC50 values of 28.4 µM, 28.3 µM, 30.7 µM, and 28.5 µM, respectively. The structure-activity relationship analysis suggested that the substructure combination of benzimidazole and naphthalene bearing the free hydroxy group at C-1 and the three methoxy groups at the C-6, C-7, and C-8 of the naphthalene ring may exhibit a synergistic effect and an improved anticancer activity.

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Published online: 11th April, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14065
An Efficient Two-Step Synthesis of 3-Aroyl-2,3-dihydro-1,4,2-benzodithiazine 1,1-Dioxides from Secondary Benzenesulfonamides, Sulfur, and Phenacyl Bromides

Kazuhiro Kobayashi* and Daiki Fujiwara

*Applied Chemistry Field, Chemistry and Biotechnology Course, Department of Engineering, Graduate School of Sustainability Science, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

An efficient method for the synthesis of 2-substituted 3-aroyl-2,3-dihydro-1,4,2-benzodithiazine 1,1-dioxides has been developed. Thus, 2,N-dilithio compounds of secondary benzenesulfonamides, generated by treating secondary benzenesulfonamides with two equivalents of butyllithium, are allowed to react with elemental sulfur and then phenacyl bromide and its derivatives to give N-substituted o-[(aroylmethyl)sulfanyl]benzenesulfonamides in moderate to good yields. Oxidative coupling of these precursors to the desired products can be achieved in moderate to good yields on successive treatment with sodium hydride and iodine under mild conditions.

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Published online: 10th April, 2019

Communication | Special issue | Prepress
DOI: 10.3987/COM-19-S(F)2
An Efficient Enantiospecific Synthesis of Neuroactive Glutamate Analogs

Shuntaro Tsukamoto, Hiyori Itagaki, Kenji Morokuma, Kei Miyako, Yuichi Ishikawa, Ryuichi Sakai, and Masato Oikawa*

*Yokohama City University, Seto 22-2, Kanazawa-ku, Yokohama 236-0027, Japan

Abstract

Herein we report improved enantiospecific synthesis and some structure-activity relationships of our heterotricyclic artificial glutamate analogs bearing seven-membered ring for the C-ring. Starting from readily available oxanorbornene rac-3, optically pure (2R)-TKM-107, (2R)-IKM-154, and the antipodes were synthesized in total nine steps for each. Mice in vivo assay indicated that only the (2R)-enantiomer was active in both cases. Behaviors phenotypes observed in the mice assay suggested that these compounds are similar in mode of action to that of IKM-159 but with discrete potency.

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Published online: 10th April, 2019

Paper | Special issue | Prepress
DOI: 10.3987/COM-19-S(F)3
Planar Chiral Phosphino[2.2]paracyclophanol-Catalyzed Highly Regio- and Stereoselective [3+2] Annulation Reaction of Morita–Baylis–Hillman Carbonates with Dicyanomethylideneoxindoles

Shinji Kitagaki,* Mayuka Tsuji, Hideki Teramoto, Naoko Takenaga, and Keisuke Yoshida

*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku-ku, Nagoya 468-8503, Japan

Abstract

To demonstrate the utility of [2.2]paracyclophane as a chiral organocatalyst backbone, we examined a planar chiral pseudo-ortho-diarylphosphino[2.2]paracyclophanol, phosphino-PCP-ol, which has a spacer aryl group between the pseudo-ortho-substituted PCP-ol backbone and the diarylphosphino group. We tested this catalyst in the [3+2] annulation reaction of MoritaBaylisHillman carbonates, derived from aromatic aldehydes and methyl acrylate, with 3-(dicyanomethylidene)-2-oxindole. The catalyst produced the desired 3-spirocyclopentene-2-oxindoles in high yields, and high regio-, diastereo-, and enantioselectivities.

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Published online: 28th March, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14044
Synthesis of N-alkyl Substituted Azasugar-tetrazole Hybrid Molecules via Ugi-azide Reaction

Hairong Luo,* Bangjian Xu, Lingyu Zhang, and Meihang Chen

*College of Material and Chemical Engineering, Tongren University, Tongren,Guizhou 554300, China

Abstract

An effective and facile method for the synthesis of N-alkyl substituted azasugar-tetrazole hybrid molecules is described. The one-pot Ugi-azide reaction provides convenient access to synthesis of α-tetrazolyl azasugar scaffolds as potential glucosidase inhibitors in moderate to good yields in methanol catalyst by lewis acid under mild conditions.

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Published online: 28th March, 2019

Additions and Corrections | Regular issue | Prepress
DOI: 10.3987/Correction-COM-15-13360
Correction to “Facile and Efficient Access to Tetrahydrobenzo[b]pyrans Catalyzed by N,N-Dimethylbenzylamine”: HETEROCYCLES, 2016, 92, 75, DOI: 10.3987/COM-15-13360

Hamzeh Kiyani* and Mozhgan Sadat Jalali

*School of Chemistry, Damghan University, 36719-41167 Damghan, Iran

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Published online: 28th March, 2019

Additions and Corrections | Regular issue | Prepress
DOI: 10.3987/Correction-COM-16-13623
Correction to “One-Pot and Efficient Synthesis of 5-Aminopyrazole-4-carbonitriles Catalyzed by Potassium Phthalimide”: HETEROCYCLES, 2017, 94, 276, DOI: 10.3987/COM-16-13623

Hamzeh Kiyani* and Maryam Bamdad

*School of Chemistry, Damghan University, 36719-41167 Damghan, Iran

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Published online: 28th March, 2019

Additions and Corrections | Regular issue | Prepress
DOI: 10.3987/Correction-COM-17-13711
Correction to “Synthesis of Erlenmeyer-Plöchl Azlactones Promoted by 5-Sulfosalicylic Acid”: HETEROCYCLES, 2017, 94, 1314, DOI: 10.3987/COM-17-13711

Hamzeh Kiyani* and Shiva Aslanpour

*School of Chemistry, Damghan University, 36719-41167 Damghan, Iran

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Published online: 28th March, 2019

Additions and Corrections | Regular issue | Prepress
DOI: 10.3987/Correction-COM-17-13847
Correction to “Sulfanilic Acid-Catalyzed Green Synthesis of 4-Arylidene-2-phenyl-5(4H)-oxazolones”: HETEROCYCLES, 2018, 96, 297, DOI: 10.3987/COM-17-13847

Hamzeh Kiyani* and Shiva Aslanpour

*School of Chemistry, Damghan University, 36719-41167 Damghan, Iran

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Published online: 27th March, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14050
Conformational Control of a Pyrrole-Based Amide Pentamer by Dihydrogen Phosphate Anion Binding

Jiulong Li, Guoping Li,* Chaocao Lu, Bu Htan, Chunmiao Ma, and Quan Gan*

*School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, China

Abstract

Conformational control is of importance for compounds to implement their properties and functions. In this work, a pyrrole-based amide pentamer 1 was synthesized. NOESY NMR experiments show it adopts two main conformations, one of which can be sorted out and stabilized via binding of a dihydrogen phosphate anion.

Supporting Info. (1.4MB)PDF (851KB)

Published online: 27th March, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14057
Visible-Light-Enabled C(sp2)H Difluoroalkylation of Aldehyde-Derived Hydrazones Under Metal-Free Conditions

Wen-Qiang Liu, Wei-Hao Chen, Xiao-Xuan Li, Wei-Ke Tang, Ting-Ting Tao, and Yi-Si Feng*

*School of Chemistry and Chemical Engineering, Hefei University of Technology, Anhui 230009, China

Abstract

A Eosin Y-catalyzed C(sp2)-H difluoromethylation of aldehyde-derived hydrazones between difluoroalkyl bromides and aldehyde-derived hydrazones is reported. This reaction has a wide range of substrates and occurs under metal-free condition. A mechanism that involves a difluoroacetate radical via single electron transfer (SET) pathway is proposed for this reaction.

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Published online: 27th March, 2019

Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14058
Diastereoselective Synthesis of 3-Alkylindoloquinolizine Derivatives via Regiospecific Oxidative Cyclization

Susana Morales-Barba, Joel L. Terán, Dino Gnecco, María L. Orea, David M. Aparicio, Víctor Gómez-Calvario, and Jorge R. Juárez*

*Centro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, Edif. IC8, Ciudad Universitaria 72570, Mexico

Abstract

3-Alkylindoloquinolizine alkaloids were synthetized in two steps from enantiopure 3-alkylpiperidines through sequential N-alkylation and regiospecific and diastereoselective oxidative cyclization.

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Published online: 27th March, 2019

Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14064
The Use of Formaldehyde in the Rhodium-Catalyzed Linear-Selective Hydroformylation of Vinylheteroarenes

Jian Pan, Tsumoru Morimoto,* Hideyuki Kobayashi, Hiroki Tanimoto, and Kiyomi Kakiuchi

*Division of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara 630-0192, Japan

Abstract

An accessible protocol for the linear-selective hydroformylation of vinylheteroarenes using formaldehyde as a substitute for syngas is reported. The simultaneous use of BIPHEP and Nixantphos ligands permitted a high regioselectivity (linear/branched = up to 93/7) and moderate yield of isolated product (up to 84%) to be obtained. Under such catalytic conditions, vinylheteroarenes containing a vinyl group at the 2-position in the heterocycle ring reacted more linear-selectively with formaldehyde than at the 3-position.

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Published online: 25th March, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-18-14029
An Efficient Synthesis of N-Aryl-2-(indol-3-yl)acetamides via Multi-Component Reactions

Guo-Ning Zhang, Mengye Zhang, Xiaonan Du, Mei Zhu, Juxian Wang,* Daqing Shi,* and Yucheng Wang*

*Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050, China

Abstract

An efficient synthesis of N-aryl-2-(indol-3-yl)acetamide derivatives via a four-component reaction of arylglyoxal monohydrate, Meldrium’s acid and anilines under microwave irradiations is described. This protocol has the advantages of high efficiency, mild reaction conditions, a one-pot procedure, and materials available.

Supporting Info. (639KB)PDF (349KB)

Published online: 25th March, 2019

Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14052
Preparation of Some Novel Trisubstituted 1,3,5-Triazines and Hybrid Linker Mode 1,3,5-Triazine Derivatives and Their Biological Evaluation

Nobuko Mibu, Kazumi Yokomizo, Kanae Yamada, Junko Matsuyama, Syoko Tomonaga, Izumi Sakai, Ryo Sato, Yuki Kawano, Yumemi Matsumoto, Yuka Fujita, Yusuke Inoue, Masaya Iida, Kaneto Hashiguchi, Jian-Rong Zhou, Makoto Furutachi, and Kunihiro Sumoto*

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan

Abstract

We report a new route to the preparation of C3-symmetrical multivalent hybrid-type molecules having a tris-aminoethylamine (TAEA) linker group and 1,3,5-triazine recognition moieties in the molecule and we also report the results of biological evaluation of their anti-herpes simplex virus type 1 (anti-HSV-1) activity and cytotoxic activity against Vero cells. Among the tested compounds, a new mid-size C2-symmetrical multivalent hybrid-type molecule (10aq) showed a high level of anti-HSV-1 activity (EC50 = 19.7 μM) with low cytotoxicity (CC50 > 200 μM) against Vero cells. A new CS-symmetrical multivalent derivative (4ab) also showed high anti-HSV-1 activity (EC50 = 1.77 μM) with low cytotoxicity (CC50 > 200 μM). The hybrid-type C2-symmetrical multivalent mid-size molecule (10aq) seems to be an interesting new lead in the search for new hybrid-type symmetrical multivalent antiviral compounds.

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Published online: 15th March, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14055
Synthesis of [1,4]Oxathiino[2,3-d]pyrimidines Starting with 4,6-Dichloro-2-(methylsulfanyl)pyrimidine

Kazuhiro Kobayashi,* Kota Yamasaki, Hidetaka Hiyoshi, and Kazuto Umezu

*Applied Chemistry Field, Chemistry and Biotechnology Course, Department of Engineering, Graduate School of Sustainability Science, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

A convenient method for the preparation of 7-(het)aryl[1,4]oxathiino[2,3-d]pyrimidine derivatives using an easily operated two-step sequence starting from 4,6-dichloro-2-(methylsulfanyl)pyrimidine (DCSMP) have been developed. Thus, the starting material is treated with LDA to generate the 5-lithio derivative, which is allowed to react with sulfur and then phenacyl bromide and its derivatives to give 1-(het)aryl-2-{[4,6-dichloro-2-(methylsulfanyl)pyrimidin-5-yl]sulfanyl}ethanones. These pyrimidinyl ketones undergo ring closure upon treatment with triethylamine to provide the corresponding desired products in reasonable overall yields from DCSMP.

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Published online: 14th March, 2019

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-19-14054
Agesamines A and B, New Dibromopyrrole Alkaloids from the Sponge Agelas sp.

Ayako Katsuki, Hikaru Kato, Yuji Ise, Fitje Losung, Remy E. P. Mangindaan, and Sachiko Tsukamoto*

*Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-hon-machi, Kumamoto 862-0973, Japan

Abstract

New dibromopyrrole alkaloids, agesamines A (1) and B (2), were obtained as an inseparable epimeric mixture from a marine sponge Agelas sp., collected in Indonesia. The planar structures were elucidated by analysis of spectroscopic data, and the absolute configuration was determined by the calculated ECD spectrum.

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82 data found. 1 - 30 listed Next Last