2S,4S-2-phenyl-5,5-dimethylthiazolidine-4-carboxylic acid | 109132-33-4

• 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,4S-2-phenyl-5,5-dimethylthiazolidine-4-carboxylic acid
• 英文别名: 5,5-dimethyl-2-phenylthiazolidine-4-carboxylic acid；5,5-dimethyl-2(S)-phenylthiazolidine-4(S)-carboxylic acid；(2S,4S)-5,5-dimethyl-2-phenyl-1,3-thiazolidin-3-ium-4-carboxylate
• CAS: 109132-33-4
• 化学式: C₁₂H₁₅NO₂S
• 分子量: 237.323
• InChiKey: LZDQTBBSEWXLTA-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  2S,4S-2-phenyl-5,5-dimethylthiazolidine-4-carboxylic acid 以 吡啶 、 乙醇 、 硫酸 、 水 为溶剂， 以0.38 g (70.3%)的产率得到(-)-(2S,4S)-3-acetyl-5,5-dimethyl-2-phenyl-4-thiazolidinecarboxylic acid
  参考文献：
  名称：

  Thiazolidinecarboxylic acid derivatives and treatment of liver diseases

  摘要：

  本发明涉及一种新型噻唑烷-4(S)-羧酸衍生物，其一般式为（I）： 其中，R1代表可选取代的呋喃基、吡咯基、噻吩基、苯并呋喃基、苯并吡咯基、苯并噻吩基、苯基、吡啶基、喹啉基、异喹啉基或茚基或C1-4烷基或C2-4烯基，可选取代羟基、羧基或卤代芬氧基；X代表氢、碱金属或碱土金属原子或可选取代的C1-4烷基或芳基；R3代表氢或可选取代的C1-4烷基或酰基或芳基，以及它们的盐。此外，本发明还涉及包含这些化合物的制药制剂以及制备这些化合物和制剂的方法。本发明的化合物可用于治疗或预防自然或实验性起源的肝损伤。

  公开号：

  US04775675A1
• 作为产物：
  描述：

  D-青霉胺 、 苯甲醛 以 乙醇 为溶剂， 反应 0.75h， 生成 2R,4S-2-phenyl-5,5-dimethylthiazolidine-4-carboxylic acid 、 2S,4S-2-phenyl-5,5-dimethylthiazolidine-4-carboxylic acid
  参考文献：
  名称：

  D-青霉胺与醛酮的相互作用：2-苯基-5,5-二甲基噻唑烷-4-羧酸

  摘要：

  D-青霉胺与苯甲醛反应生成2-苯基-5,5-二甲基噻唑烷-4-羧酸。通过单晶X射线衍射确定结构。晶体为单斜晶系，P21，a = 9.785(2)，b = 6.941(1)，c = 10.399(2) A，β = 114.06(3)°，Z = 2。强度是在 Rigaku AFC6R 衍射仪上用 Cu 测量的使用 Kα 辐射和 1881 反射来确定结构。R = 0.076，wR = 0.048。该化合物以 2S,4S 构型的氨基酸形式存在。噻唑烷环的构象由分子间氢键决定。键长和角度是正常的。1H和13C NMR谱表明差向异构发生在d4-CH3OH溶液中，室温下2S,4S非对映体与2R,4S非对映体的比例为65:35。

  DOI：

  10.1139/v94-203

文献信息

• Gyoergydeak, Zoltan; Kajtar, Judit; Kajtar, Marton, Liebigs Annalen der Chemie, 1990, p. 281 - 286
  作者：Gyoergydeak, Zoltan、Kajtar, Judit、Kajtar, Marton、Kajtar-Peredy, Maria

  DOI：——

  日期：——
• Targeting triple-negative breast cancer cells with 6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles
  作者：Kathleen Santos、Mafalda Laranjo、Ana Margarida Abrantes、Ana F. Brito、Cristina Gonçalves、Ana Bela Sarmento Ribeiro、M. Filomena Botelho、Maria I.L. Soares、Andreia S.R. Oliveira、Teresa M.V.D. Pinho e Melo

  DOI：10.1016/j.ejmech.2014.04.008

  日期：2014.5

  Further studies on 6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles as anticancer agents against breast cancer are reported, allowing to demonstrate the potential of these compounds for the therapy of the triple-negative breast cancer, the most challenging tumors in clinical practice. These compounds were assayed for their in vitro cytotoxicity on several human breast cancer cell lines (MCF7, HCC1954 and HCC1806 cell lines). Particularly interesting were the results obtained for 4-hydroxyphenyl substituted derivative, which proved to be the most promising compound regarding HCC1806 cell line, a triple-negative breast cancer. The effects of the two most active compounds on cell survival, viability, cell cycle, DNA damage and expression of proteins related to cell death pathways were studied. The reported results consolidate the potential of 6,7-bis(hydroxymethyl)-1H,3H-pyrrolo[1,2-c]thiazoles for the therapy of breast cancer, particularly the triple-negative. (c) 2014 Elsevier Masson SAS. All rights reserved.
• US4775675A
  申请人：——

  公开号：US4775675A

  公开（公告）日：1988-10-04
• The interaction of <scp>D</scp>-penicillamine with aldehydes and ketones: 2-phenyl-5,5-dimethylthiazolidine-4-carboxylic acid
  作者：R.A. Bell、J.F. Britten、H.E. Howard-Lock、C.J.L. Lock、M. Schmidt

  DOI：10.1139/v94-203

  日期：1994.7.1

  The reaction of D-penicillamine and benzaldehyde yielded 2-phenyl-5,5-dimethylthiazolidine-4-carboxylic acid. The structure was determined by single crystal X-ray diffraction. Crystals were monoclinic, P21, a = 9.785(2), b = 6.941(1), c = 10.399(2) A, β = 114.06(3)°, Z = 2. Intensities were measured on a Rigaku AFC6R diffractometer with Cu Kα radiation and 1881 reflections were used to determine the

  D-青霉胺与苯甲醛反应生成2-苯基-5,5-二甲基噻唑烷-4-羧酸。通过单晶X射线衍射确定结构。晶体为单斜晶系，P21，a = 9.785(2)，b = 6.941(1)，c = 10.399(2) A，β = 114.06(3)°，Z = 2。强度是在 Rigaku AFC6R 衍射仪上用 Cu 测量的使用 Kα 辐射和 1881 反射来确定结构。R = 0.076，wR = 0.048。该化合物以 2S,4S 构型的氨基酸形式存在。噻唑烷环的构象由分子间氢键决定。键长和角度是正常的。1H和13C NMR谱表明差向异构发生在d4-CH3OH溶液中，室温下2S,4S非对映体与2R,4S非对映体的比例为65:35。
• Thiazolidinecarboxylic acid derivatives and treatment of liver diseases
  申请人：Biogal Gyogyszergyar

  公开号：US04775675A1

  公开（公告）日：1988-10-04

  The invention relates to novel thiazolidine-4(S)-carboxylic acid derivatives of the general formula (I) ##STR1## wherein R.sup.1 stands for an optionally substituted furyl, pyrrolyl, thienyl, benzofuryl, benzopyrrolyl, benzothienyl, phenyl, pyridyl, quinolinyl, isoquinolinyl or indanyl group or a C.sub.1-4 alkyl or C.sub.2-4 alkenyl group optionally substituted by a hydroxyl, carboxyl or halogen fenoxy group, stands for hydrogen, an alkaline metal or an alkaline earth metal atom or an optionally substituted C.sub.1-4 alkyl group or aryl group; R.sup.3 represents hydrogen or an optionally substituted C.sub.1-4 alkyl or acyl group or aryl group as well as their salts. Further on, the invention relates to pharmaceutical preparations containing these compounds and to a process for preparing these compounds and preparations. The compounds of the invention are useful for treating or preventing liver damages of either natural or experimental origin.

  本发明涉及一种新型噻唑烷-4(S)-羧酸衍生物，其一般式为（I）： 其中，R1代表可选取代的呋喃基、吡咯基、噻吩基、苯并呋喃基、苯并吡咯基、苯并噻吩基、苯基、吡啶基、喹啉基、异喹啉基或茚基或C1-4烷基或C2-4烯基，可选取代羟基、羧基或卤代芬氧基；X代表氢、碱金属或碱土金属原子或可选取代的C1-4烷基或芳基；R3代表氢或可选取代的C1-4烷基或酰基或芳基，以及它们的盐。此外，本发明还涉及包含这些化合物的制药制剂以及制备这些化合物和制剂的方法。本发明的化合物可用于治疗或预防自然或实验性起源的肝损伤。