(2S,4R)-N-acetyl-2-phenyl-1,3-thiazolidine-4-carboxylic acid | 69739-24-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,4R)-N-acetyl-2-phenyl-1,3-thiazolidine-4-carboxylic acid
• 英文别名: (2S,4R) -3-acetyl-2-phenylthiazolidine-4-carboxylic acid；(2S,4R)-N-acetyl-2-phenyl-4-carboxy-1,3-thiazolidine；(4R)-3-acetyl-2t-phenyl-thiazolidine-4r-carboxylic acid；N-acetyl-N,S-(S)-benzylidene-L-cysteine；(4R)-3-Acetyl-2t-phenyl-thiazolidin-4r-carbonsaeure；(2S,4R)-3-acetyl-2-phenyl-1,3-thiazolidine-4-carboxylic acid
• CAS: 69739-24-8
• 化学式: C₁₂H₁₃NO₃S
• 分子量: 251.306
• InChiKey: NYATUQLQYZIJCY-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4R)-N-acetyl-2-phenyl-1,3-thiazolidine-4-carboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 、 乙酸酐 为溶剂， 反应 5.5h， 生成 (3S)-6,7-bis (hydroxymethyl)-5-methyl-3-phenyl-1H,3H-pyrrolo [1,2-c]thiazole
  参考文献：
  名称：

  具有抗乳腺癌特性的手性6,7-双（羟甲基）-1 H，3 H-吡咯并[1,2- c ]噻唑

  摘要：

  报道了6,7-双（羟甲基）-1 H，3 H-吡咯并[1,2- c ]噻唑类化合物作为抗MCF7乳腺癌细胞系的抗癌剂的合成及生物学评价。以（3 R）-6,7-双（羟甲基）-5-甲基-3-苯基-1 H，3 H-吡咯并[1,2- c ]噻唑为先导化合物的设计指导了新化合物的设计。化合物具有良好的抗MCF7乳腺癌细胞系性能（IC 50 = 1.0μM）。结构变化包括C-3处的苯基去除，3,4,5-三甲氧基苯基取代该基团，铅支架上C-5处的甲基去除以及该骨架的取代基团由苯基取代基取代。总体而言，这些研究表明，在1 H，3 H-吡咯并[1,2- c ]噻唑环系统中C-3处的苯基和C-5处的甲基的组合存在对于确保高细胞毒性至关重要对抗MCF7乳腺癌细胞系。为了探测前导化合物的绝对构型是否会影响其抗癌活性，制备了其对映异构体并评估了其对MCF7细胞的活性。（3 S）-6,7-双（羟甲基）-5-甲基-3-苯基-1H，3

  DOI：

  10.1016/j.ejmech.2012.11.036
• 作为产物：
  描述：

  苯甲醛 在 乙醇 、 potassium acetate 作用下， 生成 (2S,4R)-N-acetyl-2-phenyl-1,3-thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Schubert, Journal of Biological Chemistry, 1936, vol. 114, p. 348

  摘要：

  DOI：

文献信息

• Synthesis and NMR studies of thiazolidine-4-carboxylic acid derivatives containing a nitro ester function
  作者：Francesca Benedini、Francesco Ferrario、Alberto Sala、Luca Sala、Pier Angelo Soresinetti

  DOI：10.1002/jhet.5570310608

  日期：1994.11

  The preparation of thiazolidine-4-carboxylic acid derivatives containing a 2-nitrooxyethylamine group, potentially active as vasodilators, is reported. Their 1H nmr studies carried out to establish the configuration of the C2 stereocenter and the full assignment of their 1H and 13C nmr spectra, are also reported.

  据报道，含有2-硝基氧乙胺基的噻唑烷-4-羧酸衍生物的制备具有潜在的血管扩张作用。他们还进行了1 H nmr研究，以建立C2立体中心的构型，并完整报道了其1 H和13 C nmr光谱。
• [EN] "(3S)- AND (3R)-6,7-BIS(HYDROXYMETHYL)-1H,3H-PYRROLO[1,2-C]THIAZOLES AS P53 ACTIVATORS"<br/>[FR] (3S)- ET (3R)-6,7-BIS (HYDROXYMÉTHYL)-1H,3H-PYRROLO[1,2-C]THIAZOLES UTILISÉS COMME ACTIVATEURS DE P53
  申请人：UNIV DE COIMBRA

  公开号：WO2019243906A1

  公开（公告）日：2019-12-26

  The present application relates to compounds of formula I, which are (3S)- and (3R)-6,7-bis(Hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles. The present application also relates to pharmaceutical compositions comprising said compounds and the use of these compounds in the treatment of conditions influenced by wild-type or mutant p53 forms. More specifically, these compounds represent a completely new chemical family of p53-activating agents and show a higher selectivity towards the p53-pathway compared to the reactivators of p53 currently under clinical trials. For some cancer types these compounds revealed to be more potent than the reactivators of p53 currently under clinical trials. In addition to these advantages, the presently disclosed compounds are not genotoxic and have no apparent undesirable toxic side effects.

  本申请涉及的化合物属于公式I，即(3S)-和(3R)-6,7-双(羟甲基)-1H,3H-吡咯并[1,2-c]噻唑。本申请还涉及包含上述化合物的药物组合物，以及这些化合物在治疗受野生型或突变型p53形式影响的疾病中的用途。更具体地说，这些化合物代表了一种全新的p53激活剂化学家族，并显示出与目前正在临床试验中的p53再活化剂相比更高的选择性作用于p53途径。对于某些癌症类型，这些化合物显示出比目前正在临床试验中的p53再活化剂更强效的作用。除了这些优势外，目前披露的化合物不具有基因毒性，并且没有明显的不良毒性副作用。
• Heterocyclische Verbindungen aus Zuckern, XV: Zur Konfiguration chiraler C-2-substituierter 4-Thiazolidincarbons�uren. Chiralit�tstransfer auf C-3 in 3,4-Dihydro-1H-pyrrolo[1,2-c]thiazolen
  作者：Z. Gy�rgyde�k、L. Szil�gyi、J. Kajt�r、G. Argay、A. K�lm�n

  DOI：10.1007/bf00818164

  日期：1994.2

  5-Substituted 3,4-dihydro-pyrrolo[1,2-c]thiazole-6,7-dicarboxylic acid esters 3 are obtained from 2-substituted-3-acyl-1,3-thiazolidine-4-carboxylic acids, 1 in [3 + 2]-cycloaddition reactions via mesoionic oxazolone (''munchnone'') intermediates. The chirality at C-4 of the starting carboxylic acids 1 is eliminated in the products 3, and the chirality at C-3 (C-2 in the starting carboxylic acids 1) can thus be determined through chiroptical measurements. Several representatives of the ring system 3 have been characterised through H-1- and CD-spectra and the molecular structure of (3S)-3da has been determined by X-ray crystallography.
• Conformational analysis, spectral and catalytic properties of 1,3-thiazolidines, ligands for acetophenone hydrosilylation with diphenylsilane
  作者：A. N. Skvortsov、V. M. Uvarov、D. A. de Vekki、E. P. Studentsov、N. K. Skvortsov

  DOI：10.1134/s107036321010021x

  日期：2010.10

  2-Aryl- and 2-furyl-4-carboxy-1,3-thiazolidines were synthesized. Their spectral properties were studied, and conformational analysis was performed. It was shown that they exist in solution as an equilibrium of neutral and zwitter-ion forms. The influence of the nature of substitutents and of their location in a benzene ring of thiazolidines as ligands of rhodium complexes on acetophenone hydrosilylation with diphenylsilane was examined. Thiazolidines containing donor substituents in the para-position of the benzene ring were found to be the most effective; maximal asymmetrical induction (55% ee) was reached in the presence of 2-(4-methoxyphenyl)-4-carboxy-1,3-thiazolidine.
• Comments on the putative stereoselectivity in cysteine-aldehyde reactions. Selective C(2) inversion and C(4) epimerization in thiazolidine-4-carboxylic acids
  作者：Laszlo Szilagyi、Zoltan Gyorgydeak

  DOI：10.1021/ja00496a026

  日期：1979.1