(2Ξ,4R)-2-benzo[1,3]dioxol-5-yl-thiazolidine-4-carboxylic acid | 72678-96-7

• 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: (2Ξ,4R)-2-benzo[1,3]dioxol-5-yl-thiazolidine-4-carboxylic acid
• 英文别名: (2Ξ,4R)-2-Benzo[1,3]dioxol-5-yl-thiazolidin-4-carbonsaeure；(4R)-2-(1,3-benzodioxol-5-yl)-1,3-thiazolidine-4-carboxylic acid
• CAS: 72678-96-7
• 化学式: C₁₁H₁₁NO₄S
• 分子量: 253.279
• InChiKey: XFGXAJCIOOXIGL-BYDSUWOYSA-N

物化性质

• 熔点：
  182-184°C
• 沸点：
  484.7±45.0 °C(Predicted)
• 密度：
  1.473±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (2Ξ,4R)-2-benzo[1,3]dioxol-5-yl-thiazolidine-4-carboxylic acid 在 sodium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 (4R)-2-(benzo[d][1,3]dioxol-5-yl)-N-decylthiazolidine-4-carboxamide
  参考文献：
  名称：

  Synthesis and antiproliferative activity of thiazolidine analogs for melanoma

  摘要：

  We have previously described 2-aryl-thiazolidine-4-carboxylic acid amides as a novel class of antiproliferative agents for prostate cancer. Screening these compounds with melanoma cell lines revealed that several of them have potent antiproliferative activity and selectivity against melanoma. To further improve the potency and selectivity, we synthesized a new series of analogs and tested them in two melanoma cell lines and fibroblast cells (negative controls). Comparison of anticancer effects of these compounds with a standard chemotherapeutic agent, sorafenib, showed that they are very effective in killing melanoma cells with low micromolar to nanomolar antiproliferative activity and provide us a new lead for developing potential drugs for melanoma. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.05.059
• 作为产物：
  描述：

  胡椒醛 、 L-半胱氨酸盐酸盐无水物 在 乙醇 、 potassium acetate 作用下， 生成 (2Ξ,4R)-2-benzo[1,3]dioxol-5-yl-thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  2-Substituted-thiazolidine-4-carboxylic Acids

  摘要：

  DOI：

  10.1021/ja01184a520

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。
• OYA, MASAYUKI;BABA, TOSHIO;KATO, EISHIN;KAWASHIMA, YOICHI;WATANABE, TOSHI+, CHEM. AND PHARM. BULL., 1982, 30, N 2, 440-461
  作者：OYA, MASAYUKI、BABA, TOSHIO、KATO, EISHIN、KAWASHIMA, YOICHI、WATANABE, TOSHI+

  DOI：——

  日期：——
• 2-Substituted-thiazolidine-4-carboxylic Acids
  作者：Harold Soloway、Frank Kipnis、John Ornfelt、Paul E. Spoerri

  DOI：10.1021/ja01184a520

  日期：1948.4
• Synthesis and antiproliferative activity of thiazolidine analogs for melanoma
  作者：Wei Li、Yan Lu、Zhao Wang、James T. Dalton、Duane D. Miller

  DOI：10.1016/j.bmcl.2007.05.059

  日期：2007.8

  We have previously described 2-aryl-thiazolidine-4-carboxylic acid amides as a novel class of antiproliferative agents for prostate cancer. Screening these compounds with melanoma cell lines revealed that several of them have potent antiproliferative activity and selectivity against melanoma. To further improve the potency and selectivity, we synthesized a new series of analogs and tested them in two melanoma cell lines and fibroblast cells (negative controls). Comparison of anticancer effects of these compounds with a standard chemotherapeutic agent, sorafenib, showed that they are very effective in killing melanoma cells with low micromolar to nanomolar antiproliferative activity and provide us a new lead for developing potential drugs for melanoma. (c) 2007 Elsevier Ltd. All rights reserved.