(4R)-2-(4-chlorophenyl)thiazolidine-4-carboxylic acid | 198991-78-5

• 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: (4R)-2-(4-chlorophenyl)thiazolidine-4-carboxylic acid
• 英文别名: 2-(4-chlorophenyl)thiazolidine-4-carboxylic acid；(2Ξ,4R)-2-(4-chloro-phenyl)-thiazolidine-4-carboxylic acid；(2Ξ,4R)-2-(4-Chlor-phenyl)-thiazolidin-4-carbonsaeure；[4R]-2-(p-chlorophenyl)-4-thiazolidinecarboxylic acid；(R)-2-(4-chlorophenyl)thiazolidine-4-carboxylic acid；(4R)-2-(4-chlorophenyl)-1,3-thiazolidine-4-carboxylic acid
• CAS: 198991-78-5
• 化学式: C₁₀H₁₀ClNO₂S
• 分子量: 243.714
• InChiKey: LESQASCTNMKKPZ-IENPIDJESA-N

物化性质

• 沸点：
  458.3±45.0 °C(Predicted)
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R)-2-(4-chlorophenyl)thiazolidine-4-carboxylic acid 在 盐酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 3.75h， 生成
  参考文献：
  名称：

  Design, synthesis of 4-aminoquinoline-derived thiazolidines and their antimalarial activity and heme polymerization inhibition studies

  摘要：

  The present study describes the synthesis of a series of new 4-aminoquinoline-derived thiazolidines and evaluation of their antimalarial activity against a NF-54 strain of Plasmodium falciparum in vitro and N-67 strain of Plasmodium yoelii in vivo. Among the series, two compounds, 2-(4-chloro-phenyl)-thiazolidine-4-carboxylic acid [2-(7-chloro-quinolin4- ylamino)-ethyl]-amide hydrochloride (14) and 2-(2,6-dichloro-phenyl)-thiazolidine-4-carboxylic acid [2-(7-chloro-quinolin-4-ylamino)-ethyl]-amide hydrochloride (22) exhibited significant suppression of parasitaemia in the in vivo assay. All the analogues were found to form strong complex with haematin and inhibited the beta-haematin formation in vitro. These results suggest that these compounds act on heme polymerization target.

  DOI：

  10.3109/14756366.2012.666537
• 作为产物：
  描述：

  L-半胱氨酸 、 4-氯苯甲醛 以 乙醇 为溶剂， 反应 8.0h， 以78%的产率得到(4R)-2-(4-chlorophenyl)thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Synthesis, characterization and antibacterial activities of N-tert-butoxycarbonyl-thiazolidine carboxylic acid

  摘要：

  动力学选择性分辨机制是通过形成N-Boc-TCAs的分子内氢键进行亲核取代，根据Curtin-Hammett原理提出了定性解释。

  DOI：

  10.1039/c4ra15284k

文献信息

• Synthesis and antihypertensive activity of N-(mercaptoacyl)-thiazolidinecarboxylic acids.
  作者：MASAYUKI OYA、TOSHIO BABA、EISHIN KATO、YOICHI KAWASHIMA、TOSHIO WATANABE

  DOI：10.1248/cpb.30.440

  日期：——

  The synthesis and antihypertensive activity of a new series of N-(mercaptoacyl)-thiazolidinecarboxylic acids (VIIa-d) are described. Antihypertensive activity was evaluated in terms of angiotensin I-converting enzyme (ACE) inhibitory activity. The activities of these compounds were compared with that of (2S)-1-[(2S)-3-mercapto-2-methylpropanoyl] proline, SQ 14225, and many of them were found to be relatively potent inhibitors of ACE. The most potent was (4R)-2-(2-hydroxyphenyl)-3-(3-mercaptopropanoyl)-4-thiazolidinecarboxylic acid (62). Structure-activity relationships among the thiazolidines and some related compounds are discussed.

  报道了一系列新型N-(巯基乙酰基)-噻唑烷羧酸(VIIa-d)的合成及其抗高血压活性。抗高血压活性通过血管紧张素I转化酶(ACE)抑制活性来评估。这些化合物的活性与(2S)-1-[(2S)-3-巯基-2-甲基丙酰基]脯氨酸(SQ 14225)进行了比较，发现其中许多化合物是相对强效的ACE抑制剂。其中最有效的是(4R)-2-(2-羟基苯基)-3-(3-巯基丙酰基)-4-噻唑烷羧酸(62)。讨论了噻唑烷及其相关化合物的结构-活性关系。
• New aspects of the formation of 2-substituted thiazolidine-4-carboxylic acids and their thiohydantoin derivatives
  作者：Ahmed R. E. Mahdy、Elghareeb E. Elboray、Ragab F. Fandy、Hussien H. Abbas-Temirek、Moustafa F. Aly

  DOI：10.24820/ark.5550190.p009.861

  日期：——

  readily with (R)-cysteine in boiling acidified methanol to give diastereomeric mixtures of the corresponding 2-(aryl substituted) thiazolidine-4-carboxylic acids. 4-Nitrobenzaldehyde under similar conditions afforded one isomer of 2-(4-nitrophenyl)thiazolidine-4-carboxylic acid, which epimerized in the NMR solvents into a diastereomeric mixture. 2-Nitrobenzaldehyde reacted with (R)-cysteine to afford 3

  芳香醛很容易与 (R)-半胱氨酸在沸腾的酸化甲醇中反应，得到相应的 2-（芳基取代的）噻唑烷-4-羧酸的非对映异构体混合物。4-硝基苯甲醛在类似条件下得到 2-(4-硝基苯基)噻唑烷-4-羧酸的一种异构体，其在 NMR 溶剂中差向异构化为非对映异构混合物。2-硝基苯甲醛与 (R)-半胱氨酸反应得到 3,5-双-(2-硝基苯基)四氢-1H-噻唑并[3,4-c]恶唑-1-one 作为唯一产物，其在 NMR 中坍塌溶剂转化为噻唑烷-4-羧酸的非对映异构混合物。噻唑烷衍生物与异硫氰酸苯酯顺利反应，得到相应硫代乙内酰脲的单一异构体。
• Gyoergydeak, Zoltan; Kajtar-Peredy, Maria; Kajtar, Judit, Liebigs Annalen der Chemie, 1987, p. 927 - 934
  作者：Gyoergydeak, Zoltan、Kajtar-Peredy, Maria、Kajtar, Judit、Kajtar, Marton

  DOI：——

  日期：——
• Synthesis and biological evaluation of new naphthoquinone-containing pyrrolo-thiazoles as anticancer agents
  作者：Susana M. M. Lopes、Mafalda Laranjo、Arménio C. Serra、Ana Margarida Abrantes、António M. d'A. Rocha Gonsalves、Maria Filomena Botelho、Ana Matos Beja、Manuela Ramos Silva、Teresa M. V. D. Pinho e Melo

  DOI：10.1002/jhet.396

  日期：——

  Abstract magnified image Naphthoquinones undergo 1,3‐dipolar cycloaddition with bicyclic münchnones generated from thiazolidines affording new pyrrolo‐thiazoles with a fused quinone nucleus. The products were obtained as single enantiomers in good yields. These benzo[f]thiazolo[4,3‐a]isoindole‐6,11(1H,3H)‐diones are comprised of four fused rings and present a very planar structure. The evaluation of their anticancer activity against melanoma A375 and colorectal adenocarcinoma WiDr human cell lines showed only moderate activity but gave insight into the modeling of new structures. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.] J. Heterocyclic Chem., (2010).
• Dihydrithieno[2,3-b]naphto-4,9-dione analogues as anticancer agents: Synthesis and in cell pharmacological studies
  作者：Alessia Bertamino、Simona Musella、Veronica Di Sarno、Carmine Ostacolo、Michele Manfra、Daniela Vanacore、Paola Stiuso、Ettore Novellino、Pietro Campiglia、Isabel M. Gomez-Monterrey

  DOI：10.1016/j.ejmech.2015.07.044

  日期：2015.9

  The synthesis of a series of highly functionalized DNTQ-based derivatives is described. In vitro, most of the compounds exerted a cytotoxic effect against several tumour cell lines comparable to or greater than that of doxorubicin. Here we demonstrate that compound 14, the less cardiotoxic compound of this series, induced cell differentiation and was distributed mainly in the cytoplasm in the human glioblastoma LN229 cell line. Moreover, compound 14 reduced both cellular glucose uptake and serine/threonine kinase ART expression, and triggered cell apoptosis. These findings suggest that highly functionalized DTNQ-based derivatives are promising pharmacological tools for the study of human solid tumours. (C) 2015 Elsevier Masson SAS. All rights reserved.