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17 data found. 1 - 17 listed

Published online: 24th March, 2023

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-23-14828
■ (7s)-Macaureas A and B, Two Urea Analogues from the Roots of Lepidium Meyenii

Hui-Chun Geng, Shi-Yu Qiu, Shi-Wei Chen, Song-Mei Lu, Fu-Wen Yang, Ji-Rui Wei, Yong-Hui He,* and Min Zhou*

*Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming 650031, China

Abstract

(7S)-Macaureas A and B (1 and 2), two urea derivatives were isolated from the roots of Lepidium meyenii (Maca) collected from Qujing, Yunnan Province of China. Their structures were established on the basis of extensive spectroscopic data, including 1D NMR, 2D NMR and HRESIMS techniques. The absolute configuration of (−)-1 was corrected as 7S by a concise three-step synthesis from commercially available Boc-L-proline. Macaureas A and B were tested for their cytotoxicities against five human cancer cell lines.

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Published online: 23rd March, 2023

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-23-14823
■ Biotransformation of Plant Secondary Metabolites by Silkworms

Ryuhei Takeshita, Hiroaki Sasaki, Yasuhiko Matsumoto, Takashi Sugita, and Kaoru Kinoshita*

*Department of Pharmacognosy and Phytochemistry, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

Compounds resulting from the biotransformation of plant secondary metabolites by silkworms (Bombyx mori) were found in their feces. SilkMate 2S, an artificial diet, mixed with twelve powdered plant-derived crude drugs was fed to fifth instar silkworms. A glucoside was isolated from the MeOH extract of the feces ejected by the silkworms provided with Scutellariae Radix (Ogon). SilkMate 2S mixed with twelve flavonoids was fed to fifth instar silkworms. Two new compounds, 3-O-β-D-glucopyranosyloxy-6-methoxyflavone (18) and 3-O-β-D-glucopyranosyloxy-4’-hydroxyflavone (19), were obtained from the MeOH extracts of the feces ejected by the silkworms provided with 3-hydroxy-6-methoxyflavone (10) and 3,4’-dihydroxyflavone (11), respectively.

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Published online: 22nd March, 2023

Paper | Regular issue | Prepress
DOI: 10.3987/COM-23-14817
■ Stereocontrolled Synthesis of Nitrogen-Substituted Quaternary Stereogenic Centers: Lessons from a Synthetic Route to the Core Structure of Sphingofungin E

Yoshiyasu Ichikawa,* Takahiro Kinutani, Yoshimine Sakogawa, Keisuke Nakanishi, Rika Ochi, Seijiro Hosokawa, and Toshiya Masuda

*Faculty of Science, Kochi University, Akebono-cho, Kochi 780-8520, Japan

Abstract

A strategy has been developed for stereocontrolled synthesis of nitrogen-substituted quaternary stereogenic centers that utilizes enantioselective addition of diethylzinc to α,β-unsaturated aldehydes and allyl cyanate-to-isocyanate rearrangement as key steps. The power and flexibility of this approach was demonstrated by its use in a stereocontrolled synthesis of the core structure of sphingofungin E and its epimer.

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Published online: 20th March, 2023

Communication | Regular issue | Prepress
DOI: 10.3987/COM-23-14820
■ Syntheses of Two New Fluorous Crown Ethers Carrying Sugar Molecules with a Multivalent Bfp Modification: Investigations of Their Partition Ratios in Fluorous Biphasic Systems and Recyclability During Acetoxylation Reaction

Takashi Yamanoi,* Kenji Koike, Taro Koda, and Yoshiki Oda

*Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan

Abstract

This paper describes the design and synthesis of two new fluorous crown ethers (named 1 and 2) carrying sugar molecules modified with multivalent Bfp. Subsequently, we investigated their partition ratios in biphasic systems using FC 72 and several organic solvents. Then, we assessed the activities of 1 or 2 in an FC 72/acetonitrile biphasic system via the acetoxylation reaction using 2-(bromomethyl)naphthalene and potassium acetate, followed by examinations of their recyclability in a two-layer system based on their immobilization in an FC 72 solvent during the acetoxylation reactions.

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Published online: 15th March, 2023

Communication | Regular issue | Prepress
DOI: 10.3987/COM-23-14826
■ Synthesis of Maleimide-Fused Aceheptylenes from Guaiazulene

Taku Shoji,* Mayumi Uda, Tetsuo Okujima, Ryuta Sekiguchi, and Shunji Ito

*Department of Chemical Biology and Applied Chemistry, College of Engineering, Nihon University, Koriyama 963-8642, Fukushima, Japan

Abstract

Maleimide-fused aceheptylenes were prepared using guaizulene as a starting material. The condensation reaction of 3,4-diformylguaiazulene derivative, which was prepared in three steps from guaiazulene, with maleimides in the presence of tri-n-butylphosphine and 1,8-diazabicyclo[5.4.0]undec-7-ene afforded the maleimide-fused aceheptylenes. Structural feature of the aceheptylenes prepared was revealed by 1H NMR spectroscopy and nucleus-independent chemical shift calculations.

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Published online: 14th March, 2023

Paper | Regular issue | Prepress
DOI: 10.3987/COM-23-14830
■ Transnitrosation of Alicyclic N-Nitrosamines Containing Sulfur Atoms in Five- or Six-Membered Rings

Noriko Usui, Masataka Mochizuki, and Keiko Inami*

*Division of Pharmaceutical Organic Chemistry, Faculty of Pharmaceutical Sciences, Sanyo-Onoda City University, Daigakudo-ri 1-1-1, Sanyo-onoda-shi,Yamaguchi, Japan

Abstract

Nitric oxide (NO) is a cell transmitter produced in vivo. Alicyclic N-nitroso compounds serve as potential NO donors in vivo due to the formation of S-nitrosoglutathione by transnitrosation. In this study, N-nitroso compounds with a thioamide group and endocyclic sulfur atoms in 5- or 6-membered rings were synthesized and the transfer of nitroso group was analyzed. All compounds synthesized exhibited transnitrosation activity under acidic condtions. N-Nitroso-1,3-thiazinane-4-carbothioamide exhibited the highest transnitrosation activity.

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Published online: 10th March, 2023

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-23-14815
■ A Convenient Synthesis of 5-Trifluoromethyl-5-cyclopropyl-Substituted Pyrazolines

Yong-Bin Xie, Xiao-Dong Liu, Ming-Xu Zhang, Wen-Bo Chen,* Chun-Hui Xing,* and Long Lu*

*CAS Key Laboratory of Energy Regulation Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, 200032 Shanghai, China

Abstract

A new method for the preparation of 5-trifluoromethyl-5-cyclopropylpyrazoline derivatives via cesium hydroxide mediated condensation reaction of ꞵ-trifluoromethyl-ꞵ-cyclopropyl-substituted unsaturated ketones with hydrazines was reported. The approach featuring mild reaction conditions, broad substrates scope and good functional group tolerance, provided a strategy to synthesize new functionalized pyrazolines bearing both trifluoromethyl and cyclopropyl groups.

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Published online: 10th March, 2023

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-23-14824
■ Synthesis and Biological Evaluation of 5-Methylpyrimidine Derivatives as Dual Inhibitors of EGFR and Src for Cancer Treatment

Yaqing Zuo, Kehui Chen, Ying Xu, Yi Le, and Longjia Yan*

*School of Pharmaceutical Sciences, Guizhou University, Guiyang 550025, China

Abstract

In this paper, a series of new 5-methylpyrimidine derivatives was designed as dual inhibitors of EGFR and Src for cancer treatment. Twenty new compounds were synthesized and evaluated for antitumor activity with A549, HepG2, and K562 cells. Compounds 8f, 8p, and 8q showed better antitumor activity than Gefitinib and Dasatinib. They were selected for testing inhibition of EGFR and Src. The IC50 values of the most potent compound 8p was reached to 1.56 μM and 0.74 μM. In addition, the ADMET properties of compounds 8f, 8o-8q were predicted with ADMETlab 2.0.

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Published online: 10th March, 2023

Paper | Regular issue | Prepress
DOI: 10.3987/COM-23-14827
■ Synthesis of 1,2-Dicarbonyls from Five-Membered Cyclic Enamines and Arylglyoxal Hydrates under Metal-Free Conditions

Wei Fan*

*Science and Technology Office, Chuzhou City Vocation College, Chuzhou, 239000, Anhui, P. R. China

Abstract

An efficient and practical protocol for O2-enabled oxidative 1,2-dicarbonylation of five-membered cyclic enamines with arylglyoxal hydrates is developed, producing 32 examples of functionalized 1,2-dicarbonyls in good to excellent yields. Notable features of this transformation include wide substrate scope, excellent yields and metal-free conditions as well as O2 from air as the green oxidant with H2O as sole by-product.

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Published online: 9th March, 2023

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-23-14818
■ Synthesis and Photophysical Properties of Diethynylated Bibenzofuran and Benzodifuran Derivatives

Takaya Hibino and Rui Umeda*

*Faculty of Chemistry, Materials and Bioengineering, Kansai University, Suita, Osaka 564-8680, Japan

Abstract

The 3,3'-diethynyl-substituted 2,2'-bibenzofuran derivatives 1 and 3,7-diethynyl-substituted benzodifuran derivatives 2 were prepared from 1,4-bis(2-methoxyphenyl)-1,3-butadiyne and diethynyldimethoxybenzene by iodocyclization followed by Sonogashira coupling reaction, respectively.

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Published online: 9th March, 2023

Paper | Regular issue | Prepress
DOI: 10.3987/COM-23-14829
■ Synthesis and Radical Scavenging Activities of Tocopherol Analogs Containing Heterocyclic Rings

Yuta Okayama,* Masataka Mochizuki, and Keiko Inami*

*Division of Pharmaceutical Organic Chemistry, Faculty of Pharmaceutical Science, Sanyo-Onoda City University, 1-1-1 Daigakudori, Sanyo-Onoda-shi, Yamaguchi 756-0884, Japan

Abstract

Antioxidants play an essential role in preventing oxidative stress. In this study, we synthesized novel tocopherol analogs with heterocyclic rings such as quinoline (5), indole (6), and benzimidazole (7), and evaluated their radical scavenging activities. The results showed that 6 has excellent radical scavenging activity. The data suggested that radical scavenging activity was enhanced in compounds containing heterocyclic rings with sufficient π-electrons and decreased in compounds with heterocyclic rings deficient π-electrons.

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Published online: 6th March, 2023

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-23-14814
■ Chemical Structures and Cell Death Inducing Activities of the Metabolites of Aspergillus terreus

Takahiro Matsumoto,* Masaya Okayama, Hayato Yoshikawa, Shifu Maeda, Takahiro Kitagawa, and Tetsushi Watanabe*

*Department of Public Health, Kyoto Pharmaceutical University, Misasagi, Yamashina-Ku, Kyoto 607-8412, Japan

Abstract

A new steroid, terreus steroid (1), and eight known compounds (2–9) have been isolated from the airborne-derived fungus Aspergillus terreus. The structure of terreus steroid (1) was elucidated based on the chemical/physicochemical evidence. The cell death-inducing activities of the isolated compounds with or without Adriamycin (ADR) were observed using time-lapse cell imaging. Among the isolated compounds, terreus steroid (1) and territrem B (3) significantly reduced the number of mitotic entry cells at 60 μM. In addition, terreus steroid (1), territrem C (2), territrem B (3), epi-aszonalenin A (5), and methyl 3,4,5-trimethoxy-2-(2-(nicotinamido)benzamido)benzoate (6) significantly increased the number of dead cells on Adriamycin-treated HeLa cells.

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Published online: 28th February, 2023

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-23-14816
■ One-Pot Synthesis of Carbazoles by a Domino Reaction Using Microwave Heating and Antiproliferative Activities of Constituents from Murraya Plants Against Cancer Stem Cells

Kouta Ugawa, Momona Nakao, Chikako Sawada, Takahiro Matsumoto, Takahiro Kitagawa, Yutaro Ohki, Kousuke Araki, and Seikou Nakamura*

*Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan

Abstract

Carbazoles could be easily and rapidly synthesized in a one-pot synthesis using 4-methyl-1-cyclohexanone and p-anisidine in a continuous microwave-heated reaction (1 h, 140 °C). Eustifoline-B, a trace constituent of the roots of Murraya euchrestifolia, was synthesized using the carbazole derivative glycozoline obtained by this method. Next, nine carbazoles isolated from the leaves of M. koenigii and three synthetic carbazoles were evaluated for their antiproliferative activities against human astrocytoma U-251 MG cells [that is, non-cancer stem cells (non-CSCs)] and cancer stem cells (CSCs) isolated by sphere formation. Carbazoles with geranyl or prenyl moieties showed antiproliferative activity against U-251 MG CSCs. In particular, the synthetic compound eustifoline-B showed significant antiproliferative activity against U-251 MG CSCs (IC50 = 2.9 μM). Interestingly, eustifoline-B showed an approximately 10-fold higher antiproliferative activity against U-251 MG CSCs than against U-251 MG non-CSCs (IC50 = 29.4 μM).

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Published online: 24th February, 2023

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-23-14810
■ Synthesis of 2-Aryloxy-2,4,4,6,6-pentachlorocyclotriphosphazenes (N3P3Cl5(OAr)): Monoaryloxylatioin of Hexachlorocyclotriphosphazene (N3P3Cl6) and Mass Spectra of Chlorocyclotriphosphazene Derivatives. Difference between EI vs. ESI Methods

Manabu Kuroboshi,* Ryota Takahashi, and Hideo Tanaka

*Tsushima-naka 3-1-1, Kita-ku, Okayama, Okayama, Japan

Abstract

Hexachlorocyclotriphosphazene (HCCP, N3P3Cl6) was treated with Li aryloxide in THF at -40 ºC to give monoaryloxypentachlorocyclotriphosphazene (N3P3Cl5(ArO)) selectively. N3P3Cl5(ArO) did not give further aryloxylated products N3P3Cl6-n(ArO)n (n ≥ 2) under the same reaction conditions. In mass spectra (MS) of N3P3Cl5(ArO), [N3P3Cl5(ArO)]+ were detected by EI method, whereas partially hydrated products [N3P3Cl4(ArO)(O-)] were detected instead of [N3P3Cl5(ArO)]+ by ESI method.

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Published online: 9th February, 2023

Review | Regular issue | Prepress
DOI: 10.3987/REV-22-999
■ Design, Synthesis and Evaluation of Catechol-Based Amyloid Beta Aggregation Inhibitors

Hiroyuki Konno* and Kenta Teruya

*Department of Chemistry and Biological Engineering, Graduate School of Science and Engineering, Yamagata University, Yonezawa, Yamagata 992-8510, Japan

Abstract

The use of small molecules to inhibit amyloid β aggregation is one approach under investigation to prevent the onset of Alzheimer’s disease (AD). One such small molecule is curcumin, but its utility is limited by poor water solubility and hence poor bioavailability. In this review, we summarize the findings of structure-activity relationship studies of curcumin and diaryl γ-dihydropyrone, undertaken to improve their inhibitory effect and physical properties. The key findings are: phenolic hydroxy groups can be introduced at the 2 and 3,4-positions of phenol rings, the C7 spacer of curcumin is essential for good anti-amyloid β aggregation activity; and the catechol moiety is important for both anti-aggregation activity and water solubility. The combination of the C5 spacer unit and mono ketone of curcumin analogues is more effective for water solubility with high anti-amyloid β aggregation activity. Diaryl γ-dihydropyrone with hydroxy groups on phenol rings as cyclocurcumin mimetics also showed anti-amyloid β aggregation activity and high water solubility. Analogues of berberine, a benzylisoquinoline alkaloid also of interest to treat central nervous system diseases, are also reviewed. Finally, we review efforts to develop fluorescent curcumin analogues for use as diagnostic agents.

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Published online: 2nd February, 2023

Review | Regular issue | Prepress
DOI: 10.3987/REV-23-1002
■ Utility of 6-Aminouracils for Building Substituted and Heteroannulated Pyrimidines: A Comprehensive Review

Magdy A. Ibrahim, Zeinab Hussain,* Nasser M. El-Gohary, Yassin A. Gabr, Hassan A. Allimony, and Al-Shimaa Badran

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

Abstract

6-Aminouracils are very useful intermediates for building different categories of heterocyclic compounds. 6-Aminouracils are electron rich compounds due to the presence of free amino group which can initiate interactions with electron deficient centres or activate the nearby C-5 position to start the reaction followed by cyclization in most cases. The present review summarizes the different reactions developed for the synthesis of substituted and annulated pyrimidines. A diversity of substituted pyrimidines was prepared directly from reactions of 6-aminouracils with some electrophilic reagents, meanwhile formation of fused pyrimidines were
achieved by reaction of 6-aminouracils with a variety of reagents such as aromatic and aliphatic aldehydes, acyclic and cyclic methylene ketones, cyclic enols, alkynes, iminium salts and a diversity of other reagents.

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Published online: 26th January, 2023

Review | Regular issue | Prepress
DOI: 10.3987/REV-22-998
■ 3-[2-Oxo-2H-chromen-3(6)(8)-yl]-1-aryl/heteroaryl-1H-pyrazole-4-carbaldehydes: Synthesis, Reactions and Applications

Ayat K. Alsolimani, Mohammed A. Assiri, and Tarik E. Ali*

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

Abstract

The chemistry of 3-(2-oxo-2H-chromen-3(6)(8)-yl)-1-aryl/heteroaryl-1H-pyrazole-4-carbaldehydes has gained increased interest in both synthetic organic and biological fields, since a large number of developments in the use of such compounds seem to be of considerable value. This review describes all the available synthetic methods for diverse 3-(2-oxo-2H-chromen-3(6)(8)-yl)-1-aryl/ heteroaryl-1H-pyrazole-4-carbaldehydes in the literature survey. It also summarizes thier chemical behaviors as building blocks towards a variety of chemical reagents to construct related compounds as well as their biological applications.

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17 data found. 1 - 17 listed