Toluene-4-sulfonic acid 6-thiazolidin-3-yl-hexyl ester | 187977-44-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Toluene-4-sulfonic acid 6-thiazolidin-3-yl-hexyl ester
• 英文别名: 6-(1,3-Thiazolidin-3-yl)hexyl 4-methylbenzenesulfonate
• CAS: 187977-44-2
• 化学式: C₁₆H₂₅NO₃S₂
• 分子量: 343.511
• InChiKey: FINJNYIPHFVJFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid 6-thiazolidin-3-yl-hexyl ester 在 碘 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 异戊醇 、 水 、 苯 为溶剂， 反应 168.0h， 生成 2-N-[6-[2-[2-[6-[(4-amino-6,7-dimethoxyquinazolin-2-yl)-methylamino]hexylamino]ethyldisulfanyl]ethylamino]hexyl]-6,7-dimethoxy-2-N-methylquinazoline-2,4-diamine
  参考文献：
  名称：

  Synthesis and α1-antagonist activity of new prazosin- and benextramine-related tetraamine disulfides

  摘要：

  Tetraamine disulfides 1-10 were designed by combining the structural features of benextramine, an irreversible alpha(1)/alpha(2)-adrenoceptor antagonist, and prazosin, a selective competitive alpha(1)-antagonist. Their biological profile was assessed by functional and binding assays. In rat vas deferens functional experiments, tetraamine disulfides 1-10 displayed a marked selectivity at alpha(1)-adrenoceptors. Furthermore, they acted as competitive antagonists at alpha(1)-adrenoceptors and weak noncompetitive (irreversible) antagonists at alpha(2)-adrenoceptors. In binding assays, performed at alpha(1)-adrenoceptors of rat liver (alpha 1B) and submaxillary gland (alpha(1A), compound 5 showed an 11-fold selectivity for alpha(1B)-adrenoceptors in contrast to both prazosin and benextramine, which were not selective or selective for the alpha(1A)-subtype respectively.

  DOI：

  10.1016/s0223-5234(97)84357-7
• 作为产物：
  描述：

  四氢噻唑 、 1,6-bis(p-toluenesulfonyloxy)hexane 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 Toluene-4-sulfonic acid 6-thiazolidin-3-yl-hexyl ester
  参考文献：
  名称：

  Synthesis and α1-antagonist activity of new prazosin- and benextramine-related tetraamine disulfides

  摘要：

  Tetraamine disulfides 1-10 were designed by combining the structural features of benextramine, an irreversible alpha(1)/alpha(2)-adrenoceptor antagonist, and prazosin, a selective competitive alpha(1)-antagonist. Their biological profile was assessed by functional and binding assays. In rat vas deferens functional experiments, tetraamine disulfides 1-10 displayed a marked selectivity at alpha(1)-adrenoceptors. Furthermore, they acted as competitive antagonists at alpha(1)-adrenoceptors and weak noncompetitive (irreversible) antagonists at alpha(2)-adrenoceptors. In binding assays, performed at alpha(1)-adrenoceptors of rat liver (alpha 1B) and submaxillary gland (alpha(1A), compound 5 showed an 11-fold selectivity for alpha(1B)-adrenoceptors in contrast to both prazosin and benextramine, which were not selective or selective for the alpha(1A)-subtype respectively.

  DOI：

  10.1016/s0223-5234(97)84357-7

文献信息

• Synthesis and α1-antagonist activity of new prazosin- and benextramine-related tetraamine disulfides
  作者：D Giardinà、M Crucianelli、U Gulini、G Marucci、C Melchiorre、S Spampinato

  DOI：10.1016/s0223-5234(97)84357-7

  日期：1997.1

  Tetraamine disulfides 1-10 were designed by combining the structural features of benextramine, an irreversible alpha(1)/alpha(2)-adrenoceptor antagonist, and prazosin, a selective competitive alpha(1)-antagonist. Their biological profile was assessed by functional and binding assays. In rat vas deferens functional experiments, tetraamine disulfides 1-10 displayed a marked selectivity at alpha(1)-adrenoceptors. Furthermore, they acted as competitive antagonists at alpha(1)-adrenoceptors and weak noncompetitive (irreversible) antagonists at alpha(2)-adrenoceptors. In binding assays, performed at alpha(1)-adrenoceptors of rat liver (alpha 1B) and submaxillary gland (alpha(1A), compound 5 showed an 11-fold selectivity for alpha(1B)-adrenoceptors in contrast to both prazosin and benextramine, which were not selective or selective for the alpha(1A)-subtype respectively.