(2RS,4R)-2-phenylthiazolidine-4-carboxylic acid octadecylamide | 849052-32-0

• 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: (2RS,4R)-2-phenylthiazolidine-4-carboxylic acid octadecylamide
• 英文别名: (4R)-2-phenyl-thiazolidine-4-carboxylic acidoctadecylamide；(4R)-N-Octadecyl-2-phenyl-4-thiazolidinecarboxamide；(4R)-N-octadecyl-2-phenyl-1,3-thiazolidine-4-carboxamide
• CAS: 849052-32-0
• 化学式: C₂₈H₄₈N₂OS
• 分子量: 460.768
• InChiKey: HUVABQXVXBSPIS-QODXOHEASA-N

物化性质

• 沸点：
  624.6±55.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  32
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 生成 (2RS,4R)-2-phenylthiazolidine-4-carboxylic acid octadecylamide
  参考文献：
  名称：

  抗癌药物2-芳基噻唑烷-4-甲酰胺的合成、体外构效关系及体内研究

  摘要：

  合成了一系列(2RS , 4R ) -2-芳基噻唑烷-4-甲酰胺(ATCAA)。与对照细胞（分别为成纤维细胞和 RH7777）相比，评估了针对黑色素瘤和前列腺癌细胞的抗增殖活性。化合物3id对三种黑色素瘤细胞系（B16-F1、A375 和 WM-164）表现出最佳的选择性和生长抑制活性。化合物15b和3ac对四种前列腺癌细胞系（DU 145、PC-3、LNCaP 和 PPC-1）具有良好的选择性和效力。讨论了侧链、噻唑烷环和苯基取代基的构效关系（SAR）。细胞周期分析表明，用1b和3ad处理后，发生凋亡（亚 G1 期）的癌细胞百分比增加，这也强烈抑制了黑色素瘤集落的形成。对带有 A375 黑色素瘤肿瘤的裸鼠的体内研究表明，化合物1b以剂量依赖性方式抑制肿瘤生长。在 10 mg/kg 的剂量下，1b显着抑制黑色素瘤肿瘤的生长，并且比 60 mg/kg 的达卡巴嗪显示出更高的疗效。

  DOI：

  10.1016/j.bmc.2009.12.020

文献信息

• THIAZOLIDINONE AMIDES, THIAZOLIDINE CARBOXYLIC ACID AMIDES, AND SERINE AMIDES, INCLUDING POLYAMINE CONJUGATES THEREOF, AS SELECTIVE ANTI-CANCER AGENTS
  申请人：Miller Duane D.

  公开号：US20080255213A1

  公开（公告）日：2008-10-16

  Substituted thiazolidinone carboxylic acid amides and substituted thiazolidine carboxylic acid amides having a structure where the various substituent groups are as defined in the specification. Methods of making these compounds, pharmaceutical compositions containing the compounds, and their use, particularly for treating or preventing cancer, are also disclosed.

  具有结构的取代噻唑烷酮羧酸酰胺和取代噻唑烷羧酸酰胺，其中各种取代基如规范中定义。还披露了制备这些化合物的方法、含有这些化合物的药物组合物，以及它们的用途，特别是用于治疗或预防癌症。
• [EN] THIAZOLIDINONE AMIDES, THIAZOLIDINE CARBOXYLIC ACID AMIDES, METHODS OF MAKING, AND USES THEREOF<br/>[FR] AMIDES DE THIAZOLIDINONE, AMIDES D'ACIDE CARBOXYLIQUE DE THIAZOLIDINE, PROCEDES DE FABRICATION ET UTILISATIONS CORRESPONDANTS
  申请人：UNIV TENNESSEE RES FOUNDATION

  公开号：WO2005049591A1

  公开（公告）日：2005-06-02

  Substituted thiazolidinone carboxylic acid amides and substituted thiazolidine carboxylic acid amides according to formulae (I) and (II) are disclosed where the various substituent groups are as defined in the specification. Methods of making these compounds, pharmaceutical compositions containing the compounds, and their use, particularly for treating or preventing cancer, are also disclosed.

  根据公式(I)和(II)披露了替代噻唑烷酮羧酸酰胺和替代噻唑烷羧酸酰胺，其中各种取代基如规范中所定义。还披露了制备这些化合物的方法，含有这些化合物的药物组合物，以及它们的用途，特别是用于治疗或预防癌症。
• Analogs exhibiting inhibition of cell proliferation, methods of making, and uses thereof
  申请人：Miller D. Duane

  公开号：US20060014740A1

  公开（公告）日：2006-01-19

  Analogs exhibiting inhibition of cell proliferation are provided. Methods of making the analogs are also included. The analogs can be used to treat cancerous conditions such as prostate, breast, and ovarian cancer.

  提供了抑制细胞增殖的类似物。方法包括制备这些类似物。这些类似物可用于治疗癌症状况，如前列腺癌、乳腺癌和卵巢癌。
• Thiazolidinone amides, thiazolidine carboxylic acid amides, methods of making, and uses thereof
  申请人：Miller D. Duane

  公开号：US20060040998A1

  公开（公告）日：2006-02-23

  Substituted thiazolidinone carboxylic acid amides and substituted thiazolidine carboxylic acid amides according to formulae (I) and (II) are disclosed where the various substituent groups are as defined in the specification. Methods of making these compounds, pharmaceutical compositions containing the compounds, and their use, particularly for treating or preventing cancer, are also disclosed.

  本发明公开了根据式（I）和（II）的取代噻唑啉酮羧酸酰胺和取代噻唑啉羧酸酰胺，其中各种取代基团如规范中所定义。还公开了制备这些化合物的方法、含有这些化合物的药物组合物以及它们的用途，特别是用于治疗或预防癌症。
• THIAZOLIDINONE AMIDES, THIAZOLIDINE CARBOXYLIC ACID AMIDES, METHODS OF MAKING, AND USES THEREOF
  申请人：Miller Duane D.

  公开号：US20090143446A1

  公开（公告）日：2009-06-04

  Substituted thiazolidinone carboxylic acid amides and substituted thiazolidine carboxylic acid amides according to formulae (I) and (II) are disclosed where the various substituent groups are as defined in the specification. Methods of making these compounds, pharmaceutical compositions containing the compounds, and their use, particularly for treating or preventing cancer, are also disclosed.

  本发明揭示了按式（I）和（II）公式的取代噻唑啉酮羧酸酰胺和取代噻唑啉羧酸酰胺，其中各种取代基团如规范中所定义。还揭示了制备这些化合物的方法，含有这些化合物的药物组合物以及它们的用途，特别是用于治疗或预防癌症。