Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide.

Rahman VP; Mukhtar S; Ansari WH; Lemiere G

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Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide.

机译：10-十一碳烯酸酰肼中一些新颖的长烷基链取代的噻唑烷酮-4-酮和噻唑-4-酮的合成，立体化学和生物活性。

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The synthesis of four novel compounds, (i) [(11-{[2-(3-nitrophenyl)-4-oxo-1,3-thiazolidin-3-yl]amino}-11-oxoundecyl)s ulfanyl]acetic acid (4), (ii) N-[5-methyl-2-(3-nitrophenyl)-4-oxo-1,3-thiazolidin-3-yl]undec-10-enamide (5), (iii) 2-[(11-{[5-methyl-2-(3-nitrophenyl)-4-oxo-1,3-thiazolidin-3-yl]amino}-11-o xoundecyl)sulfanyl]propanoic acid (6) and (iv) 3-[(11-{[2-(3-nitrophenyl)-4-oxo-1,3-thiazinan-3-yl]amino}-11-oxoundecenyl ) sulfanyl]propanoic acid (8) from 10-undecenoic acid hydrazide (1) via m-nitrobenzaldehyde-10-undecenohydrazone (2) using mercaptoacetic acid in (i), 2-mercaptopropionic acid in (ii and iii) and 3-mercaptopropionic acid in (iv) is described. The uncyclized products, ({11-[(2E)-2-(3-nitrobenzylidene)hydrazino]-11-oxo-undecyl}sulfanyl)acetic acid (3) and 3-({11-[(2E)-2-(3-nitrobenzylidene)hydrazino]-11-oxoundecyl}sulfanyl)propa noic acid (7) are also obtained in (i) and (iv), respectively. The hydrazones (2), (3) and (7) exist in two conformers as synperiplanar and antiperiplanar. Structural assignment, stereochemistry and biological assays are discussed.

机译：四种新型化合物的合成，（i）[（11-{[2-（3-硝基苯基）-4-氧代-1,3-噻唑烷-3-基]氨基} -11-氧杂环戊基）硫烷基]乙酸（4），（ii）N- [5-甲基-2-（3-硝基苯基）-4-氧代-1，3-噻唑烷-3-基]十一碳烯-10-酰胺（5），（iii）2- [（11-{[5-甲基-2-（3-硝基苯基）-4-氧代-1,3-噻唑烷-3-基]氨基} -11-邻苯二基）硫烷基]丙酸（6）和（iv ）10-十一碳烯酸中的3-[（11-{[2-（3-硝基苯基）-4-氧代-1,3-噻嗪南-3-基]氨基} -11-氧杂烯基）硫烷基]丙酸（8）描述了使用（i）中的巯基乙酸，（ii和iii）中的2-巯基丙酸和（iv）中的3-巯基丙酸通过间硝基苯甲醛-10-十一碳hydr（2）生成酰肼（1）。未环化的产物（{11-[（（2E）-2-（3-硝基亚苄基）肼基] -11-氧-十一烷基}硫烷基）乙酸（3）和3-（{{11-[（2E）-2- （3-硝基亚苄基）肼基] -11-氧杂癸基}硫烷基）丙酸（7）也分别在（i）和（iv）中获得。（2），（3）和（7）以顺平面和反平面的两个构象形式存在。讨论了结构分配，立体化学和生物学分析。

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《European Journal of Medicinal Chemistry: Chimie Therapeutique》 |2005年第2期|共12页
作者
Rahman VP; Mukhtar S; Ansari WH; Lemiere G;
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正文语种 eng
中图分类基础医学;
关键词
Acids; novel; Stereochemistry; Synthesis; 酸类;

机译：Acids;novel;Stereochemistry;Synthesis;酸类;

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1. Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide. [J] . Rahman VP, Mukhtar S, Ansari WH, European Journal of Medicinal Chemistry: Chimie Therapeutique . 2005,第2期

机译：10-十一碳烯酸酰肼中一些新颖的长烷基链取代的噻唑烷酮-4-酮和噻唑-4-酮的合成，立体化学和生物活性。
2. Antifungal Activities of Some 2-(P-Substituted Benzylidene)-3-(5-Alkyl-1, 3, 4-Thiadiazol-2-Yl) Thiazolidin-4-Ones [J] . Sunil Kumar Der Pharmacia Lettre . 2019,第1期

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3. Synthesis and biological activity of 2-(3′-hydroxypropylidene)- 1α-hydroxy-19-norvitamin D analogues with shortened alkyl side chains [J] . Glebocka A., Sicinski R.R., Plum L.A., Journal of Medicinal Chemistry . 2011,第19期

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4. Synthesis and characterization of some sulphonamidic compounds, derivatives of 4-chloro-3- (N-alkyl/ aril-sulphonamido)-benzoic acid, with potential biologic activity [C] . Simona Gabriela Hora, Georgeta Simu, D. Fara, 12th Romanian International Conference on Chemistry and Chemical Engineering Sep 13-15, 2001 Bucharest, Romania . 2001

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机译：第一部分。Baylis-Hillman反应产物2-羟甲基丙烯酸在合成新型N骨架至侧链环状肽类似物中的应用：策略和副反应。第二部分具有与4-苯胺基-n-苯乙基-哌啶偶联的氨基酸的嵌合生物活性肽的合成和生物活性。
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7. Synthesis, characterization and biological activity of new series 2-azobenzen-3- (substituted phenyl) thiazolidin-4-one [O] . 2016

机译：新系列的合成，表征和生物活性2-壬苯-3-（取代苯基）噻唑烷-4-一体化

Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide.

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