3-苯甲酰基-1,3-噻唑烷-2-羧酸 | 114199-22-3

• 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
• 中文名称: 3-苯甲酰基-1,3-噻唑烷-2-羧酸
• 英文名称: 3-benzoylthiazolidine-2-carboxylic acid
• 英文别名: 2-Thiazolidinecarboxylic acid, 3-benzoyl-；3-benzoyl-1,3-thiazolidine-2-carboxylic acid
• CAS: 114199-22-3
• 化学式: C₁₁H₁₁NO₃S
• 分子量: 237.279
• InChiKey: MJTVVARFPCSOGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  3-苯甲酰基-1,3-噻唑烷-2-羧酸 在 lithium aluminium tetrahydride 、 乙酸酐 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 [5-phenyl-7-(propan-2-ylcarbamoyloxymethyl)-2,3-dihydropyrrolo[2,1-b][1,3]thiazol-6-yl]methyl N-propan-2-ylcarbamate
  参考文献：
  名称：

  Synthesis and antineoplastic activity of 5-aryl-2,3-dihydropyrrolo[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates)

  摘要：

  A series of 1-thia analogues of the pyrrolizine bis(carbamate) 9 (NSC-278214), namely 5-aryl-2,3-dihydropyrrolo-[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates) (7a-d), were prepared by multistep syntheses from the proline analogue thiazolidine-2-carboxylic acid. The compounds were tested for growth inhibitory activity with the HL-60 human promyelocytic leukemia cell line. Three of the compounds had antileukemic activity equal to that of 9, while a 4-chlorophenyl analogue was approximately 75% more potent. A simple aromatic derivative, 1,2-benzenedimethanol 1,2-bis(isopropylcarbamate) (8), had no activity in this system. Antitumor activity was also tested in a colony formation assay with HT-29 human colon carcinoma cells. Compounds 7a-d reduced relative cell survival by over 3 logs at a concentration of 300 microM (2-h exposure), while a comparable inhibition was observed with 150 microM 9. Hence compounds 7a-d retain significant antineoplastic activity.

  DOI：

  10.1021/jm00402a030
• 作为产物：
  描述：

  噻唑烷-2-甲酸 、 苯甲酰氯 在 sodium hydroxide 作用下， 以97%的产率得到3-苯甲酰基-1,3-噻唑烷-2-羧酸
  参考文献：
  名称：

  Synthesis and antineoplastic activity of 5-aryl-2,3-dihydropyrrolo[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates)

  摘要：

  A series of 1-thia analogues of the pyrrolizine bis(carbamate) 9 (NSC-278214), namely 5-aryl-2,3-dihydropyrrolo-[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates) (7a-d), were prepared by multistep syntheses from the proline analogue thiazolidine-2-carboxylic acid. The compounds were tested for growth inhibitory activity with the HL-60 human promyelocytic leukemia cell line. Three of the compounds had antileukemic activity equal to that of 9, while a 4-chlorophenyl analogue was approximately 75% more potent. A simple aromatic derivative, 1,2-benzenedimethanol 1,2-bis(isopropylcarbamate) (8), had no activity in this system. Antitumor activity was also tested in a colony formation assay with HT-29 human colon carcinoma cells. Compounds 7a-d reduced relative cell survival by over 3 logs at a concentration of 300 microM (2-h exposure), while a comparable inhibition was observed with 150 microM 9. Hence compounds 7a-d retain significant antineoplastic activity.

  DOI：

  10.1021/jm00402a030

文献信息

• [2+2] Cycloaddition Reactions of Imines with Cyclic Ketenes: Synthesis of 1,3-Thiazolidine Derived Spiro-β-lactams and Their Transformations
  作者：Giuseppe Cremonesi、Piero Dalla Croce、Concetta La Rosa

  DOI：10.1002/hlca.200590125

  日期：2005.6

  Unsymmetric cyclic ketenes were generated from N-acyl-1,3-thiazolidine-2-carboxylic acids 1a–c by means of Mukaiyama's reagent, and then reacted with imines 2a–c to the new, isomeric spiro-β-lactams 3 and 4via [2+2] cycloaddition (Staudinger ketene–imine reaction; Scheme 1). The reactions were stereoselective (Table 1) and mainly afforded the spiro-β-lactams with a relative trans configuration. The

  N-酰基-1,3-噻唑烷-2-羧酸1a - c通过Mukaiyama试剂生成不对称环状烯酮，然后与亚胺2a - c反应生成新的异构螺-β-内酰胺3和4通过[2 + 2]环加成反应（Staudinger酮-亚胺反应；方案1）。反应是立体选择性的（表1），并且主要提供具有相对反式构型的螺-β-内酰胺。螺旋β可以通过噻唑烷开环将β-内酰胺转化为相应的单环β-内酰胺，或者通过水解β-内酰胺环将其转化为取代的噻唑烷。
• Synthesis of imidazo[5,1-b]thiazoles or spiro-β-lactams by reaction of imines with mesoionic compounds or ketenes generated from N-acyl-thiazolidine-2-carboxylic acids
  作者：Giuseppe Cremonesi、Piero Dalla Croce、Concetta La Rosa

  DOI：10.1016/j.tet.2003.10.093

  日期：2004.1

  New mesoionic compounds (2H, 3H-thiazolo[3,2-c]oxazol-7-ones) (beta) or ketenes ((3-acyl-1,3-thiazolidin-2-ylidene)methanone) (beta') were generated from N-acetyl and N-benzoyl-thiazolidine-2-carboxylic acids (7a,b) using different methods, and their reactivity towards N-(phenylmethylene)benzenesulfonamide (2) and N-(phenylmethylene)aniline (3) was tested. When (7a,b) were treated with (2) and acetic anhydride in refluxing toluene solution, only imidazo[5,1-b]thiazoles (8a,b) were obtained from the mesoionic compound intermediates (beta). When the ketene intermediates (beta') were generated from (7a,b) by means of Mukaiyama's reagent, only spiro-beta-lactams (9a,b) were isolated. (C) 2003 Elsevier Ltd. All rights reserved.
• LALEZARI, IRAJ;SCHWARTZ, EDWARD L., J. MED. CHEM., 31,(1988) N 7, 1427-1429
  作者：LALEZARI, IRAJ、SCHWARTZ, EDWARD L.

  DOI：——

  日期：——
• Compounds having an antidote activity for the protection of cultivations of agrarian interest from the action of nonselective herbicides
  申请人：Montedison S.p.A.

  公开号：EP0104495B1

  公开（公告）日：1988-11-30
• Synthesis and antineoplastic activity of 5-aryl-2,3-dihydropyrrolo[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates)
  作者：Iraj Lalezari、Edward L. Schwartz

  DOI：10.1021/jm00402a030

  日期：1988.7

  A series of 1-thia analogues of the pyrrolizine bis(carbamate) 9 (NSC-278214), namely 5-aryl-2,3-dihydropyrrolo-[2,1-b]thiazole-6,7-dimethanol 6,7-bis(isopropylcarbamates) (7a-d), were prepared by multistep syntheses from the proline analogue thiazolidine-2-carboxylic acid. The compounds were tested for growth inhibitory activity with the HL-60 human promyelocytic leukemia cell line. Three of the compounds had antileukemic activity equal to that of 9, while a 4-chlorophenyl analogue was approximately 75% more potent. A simple aromatic derivative, 1,2-benzenedimethanol 1,2-bis(isopropylcarbamate) (8), had no activity in this system. Antitumor activity was also tested in a colony formation assay with HT-29 human colon carcinoma cells. Compounds 7a-d reduced relative cell survival by over 3 logs at a concentration of 300 microM (2-h exposure), while a comparable inhibition was observed with 150 microM 9. Hence compounds 7a-d retain significant antineoplastic activity.