2R,4S-2-phenyl-5,5-dimethylthiazolidine-4-carboxylic acid | 133209-48-0

• 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: 2R,4S-2-phenyl-5,5-dimethylthiazolidine-4-carboxylic acid
• 英文别名: 5,5-dimethyl-2-phenylthiazolidine-4-carboxylic acid；(2R,4S)-5,5-dimethyl-2-phenyl-1,3-thiazolidine-4-carboxylic acid
• CAS: 133209-48-0
• 化学式: C₁₂H₁₅NO₂S
• 分子量: 237.323
• InChiKey: LZDQTBBSEWXLTA-VHSXEESVSA-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

• 作为产物：
  描述：

  D-青霉胺 、 苯甲醛 在 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以41%的产率得到2R,4S-2-phenyl-5,5-dimethylthiazolidine-4-carboxylic acid
  参考文献：
  名称：

  2R,4S-2-(2′-Methyl-3′-hydroxy-5′-hydroxymethylenepyridine-C4′)-5,5-dimethylthiazolidine-4-carboxylic acid, the product of the reaction of D-penicillamine and vitamin B6

  摘要：

  我们研究了D-和L-青霉胺与吡哆醛盐酸盐的反应，并通过单晶X射线衍射检查了产物。确定了由D-青霉胺和吡哆醛反应形成的标题化合物A的结构。晶体为正交晶系，P2₁2₁2₁，晶胞参数为a = 9.507(5) Å，b = 19.185(5) Å，c = 7.766(2) Å，Z = 4。该结构是通过标准方法解决的，并对2433个独立反射进行了精细的修正，R = 0.088，R_w = 0.079。A存在于离子态，并且键长和键角是正常的。在固态中，A和由L-青霉胺得到的相应产物B具有相同的几何结构，但手性相反；也就是说，D-青霉胺产生2R,4S对映异构体，L-青霉胺产生2S,4R对映异构体（没有S,S和R,R成分）。然而，在溶液中，NMR谱表明存在两对对映异构体（2R,4S和2S,4S；2S,4R和2R,4R）。在中性或碱性溶液中，似乎在连接到吡哆醛基团的噻唑烷碳原子处存在快速的外消旋反应。还讨论了质谱、¹H NMR、振动和电子光谱的特征。关键词：D-青霉胺、维生素B6、吡哆醛盐酸盐、治疗用途、双化学反应、结构。

  DOI：

  10.1139/v91-001

文献信息

• 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。
• 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.
• 2<i>R</i>,4<i>S</i>-2-(2′-Methyl-3′-hydroxy-5′-hydroxymethylenepyridine-C4′)-5,5-dimethylthiazolidine-4-carboxylic acid, the product of the reaction of <scp>D</scp>-penicillamine and vitamin B6
  作者：R. Faggiani、H. E. Howard-Lock、C. J. L. Lock、R. Orgias

  DOI：10.1139/v91-001

  日期：1991.1.1

  We have studied the reaction of both D- and L-penicillamine with pyridoxal hydrochloride and examined the products by single crystal X-ray diffraction. The structure of the title compound, A, formed by the reaction of D-penicillamine and pyridoxal was determined. Crystals are orthorhombic, P2₁2₁2₁, with cell dimensions a = 9.507(5), b = 19.185(5), c = 7.766(2) Å and Z = 4. The structure was solved by standard methods and refined to R = 0.088, R_w = 0.079 for 2433 independent reflections. A exists as a zwitterion, and bond lengths and angles are normal. In the solid state, A and the corresponding product obtained from L-penicillamine, B, have identical geometrical structure but are of opposite chirality; that is, D-penicillamine produces the 2R,4S diastereomer and L-penicillamine produces the 2S,4R diastereomer (with no S,S and R,R components). In solution, however, NMR spectra show the presence of both pairs of diastereomers (2R,4S and 2S,4S; 2S,4R and 2R,4R). In neutral or alkaline solution there appears to be a rapid epimerization at the thiazolidine carbon atom attached to the pyridoxal moiety. Features of the mass, ¹H NMR, vibrational, and electronic spectra are also discussed. Key words: D-penicillamine, vitamin B6, pyridoxal hydrochloride, therapeutic uses, bischemical reactions, structures.

  我们研究了D-和L-青霉胺与吡哆醛盐酸盐的反应，并通过单晶X射线衍射检查了产物。确定了由D-青霉胺和吡哆醛反应形成的标题化合物A的结构。晶体为正交晶系，P2₁2₁2₁，晶胞参数为a = 9.507(5) Å，b = 19.185(5) Å，c = 7.766(2) Å，Z = 4。该结构是通过标准方法解决的，并对2433个独立反射进行了精细的修正，R = 0.088，R_w = 0.079。A存在于离子态，并且键长和键角是正常的。在固态中，A和由L-青霉胺得到的相应产物B具有相同的几何结构，但手性相反；也就是说，D-青霉胺产生2R,4S对映异构体，L-青霉胺产生2S,4R对映异构体（没有S,S和R,R成分）。然而，在溶液中，NMR谱表明存在两对对映异构体（2R,4S和2S,4S；2S,4R和2R,4R）。在中性或碱性溶液中，似乎在连接到吡哆醛基团的噻唑烷碳原子处存在快速的外消旋反应。还讨论了质谱、¹H NMR、振动和电子光谱的特征。关键词：D-青霉胺、维生素B6、吡哆醛盐酸盐、治疗用途、双化学反应、结构。