tert-butyl (2S,4S)-2-hydroxymethyl-4-((phenylsulfonyl)amino)-pyrrolidine-1-carboxylate | 121148-11-6

• 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: tert-butyl (2S,4S)-2-hydroxymethyl-4-((phenylsulfonyl)amino)-pyrrolidine-1-carboxylate
• 英文别名: (2S,4S)-1-t-butoxycarbonyl-2-hydroxymethyl-4-phenylsulfonylaminopyrrolidine；tert-butyl (2S,4S)-4-(benzenesulfonamido)-2-(hydroxymethyl)pyrrolidine-1-carboxylate
• CAS: 121148-11-6
• 化学式: C₁₆H₂₄N₂O₅S
• 分子量: 356.443
• InChiKey: YTMYKOCTVAVKGK-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,4S)-2-hydroxymethyl-4-((phenylsulfonyl)amino)-pyrrolidine-1-carboxylate 在 吡啶 、 chromium(VI) oxide 、 Celite 、 sodium hydride 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 7.0h， 生成 (5E/Z)-6-((2S,4S)-1-(tert-butoxycarbonyl)-4-((phenylsulfonyl)amino)pyrrolidin-2-yl)-5-hexenoic acid
  参考文献：
  名称：

  Synthesis and Biological Activity of 1-Phenylsulfonyl-4-Phenylsulfonylaminopyrrolidine Derivatives as Thromboxane A 2 Receptor Antagonists

  摘要：

  The synthesis and biological activity of novel 1-phenylsulfonyl-4- phenylsulfonylaminopyrrolidine analogues are described. All compounds were produced through modification of the substituent formally corresponding to the 1,3-dioxane ring system and the omega-octenol side chain of thromboxane A(2) (TXA(2)), in reference to the structure of Daltroban. Several compounds were found to be potent TXA(2) receptor antagonists. Compound 51a was the most effective inhibitor of 9.11-epoxymethano PGH(2) (U-46619)-induced rat aortic strip contraction (IC50 = 0.48 nM). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00397-2
• 作为产物：
  描述：

  L-羟基脯氨酸 在 palladium on activated charcoal 氯化亚砜 、 sodium azide 、 氢气 、 二异丁基氢化铝 、 三乙胺 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， -25.0~90.0 ℃ 、303.98 kPa 条件下， 反应 25.0h， 生成 tert-butyl (2S,4S)-2-hydroxymethyl-4-((phenylsulfonyl)amino)-pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis and Biological Activity of 1-Phenylsulfonyl-4-Phenylsulfonylaminopyrrolidine Derivatives as Thromboxane A 2 Receptor Antagonists

  摘要：

  The synthesis and biological activity of novel 1-phenylsulfonyl-4- phenylsulfonylaminopyrrolidine analogues are described. All compounds were produced through modification of the substituent formally corresponding to the 1,3-dioxane ring system and the omega-octenol side chain of thromboxane A(2) (TXA(2)), in reference to the structure of Daltroban. Several compounds were found to be potent TXA(2) receptor antagonists. Compound 51a was the most effective inhibitor of 9.11-epoxymethano PGH(2) (U-46619)-induced rat aortic strip contraction (IC50 = 0.48 nM). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00397-2

文献信息

• Pyrrolidine derivatives as antiasthmatics
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04916152A1

  公开（公告）日：1990-04-10

  The invention relates to novel compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, lower alkoxycarbonyl, phenylsulfonyl, phenylsulfonyl substituted with 1 to 3 substituent(s) selected from the group consisting of halogen, nitro, lower alkoxy, mono (or di or tri)halo(lower)alkyl and lower alkyl, phenylcarbamoyl, lower alkylsulfonyl, benzoyl or thienylsulfonyl; R.sup.2 is phenylsulfonyl or phenylsulfonyl substituted with 1 to 3 substituent(s) selected from the group consisting of halogen, lower alkyl, lower alkoxy and mono(or di or tri)halo(lower)alkyl, R.sup.3 is carboxy(lower)alkyl, lower alkyl substituted with carboxy and 1 to 3 halogen atom(s), esterified carboxy(lower)alkyl, carbamoyl(lower)alkyl, lower alkylsulfonylcarbamoyl(lower)alkyl, phenylsulfonylcarbamoyl(lower)alkyl, carboxyphenyl, esterified carboxyphenyl, carboxy, esterified carboxy, hydroxy(lower)alkyl, sulfino(lower)alkyl, phosphono(lower)alkyl, di(lower)alkoxyphosphoryl(lower)alkyl or halo(lower)alkyl, R.sup.7 is hydrogen or lower alkyl, and A is ##STR2## in which R.sup.8 is hydrogen or lower alkyl, or a pharmaceutically acceptable salt thereof, useful as therapeutic agents for thrombosis, asthma and nephritis.

  本发明涉及新型化合物的公式：##STR1##其中R.sup.1是氢，低碳酰氧基，苯基磺酰基，苯基磺酰基，其上被1至3个取代基取代，所述取代基选自卤素，硝基，低烷氧基，单（或双或三）卤（低）烷基和低烷基，苯基氨基甲酰基，低烷基磺酰基，苯甲酰基或噻吩基磺酰基; R.sup.2是苯基磺酰基或苯基磺酰基，其上被1至3个取代基取代，所述取代基选自卤素，低烷基，低烷氧基和单（或双或三）卤（低）烷基，R.sup.3是羧基（低）烷基，低烷基，其上被羧基和1至3个卤素原子取代，酯化的羧基（低）烷基，氨基甲酰（低）烷基，低烷基磺酰氨基甲酰（低）烷基，苯基磺酰氨基甲酰（低）烷基，羧基苯基，酯化的羧基苯基，羧基，酯化的羧基，羟基（低）烷基，磺酰基（低）烷基，膦酸（低）烷基，二（低）烷氧基磷酰基（低）烷基或卤（低）烷基，R.sup.7是氢或低烷基，A是##STR2##其中R.sup.8是氢或低烷基，或其药学上可接受的盐，用作治疗血栓，哮喘和肾炎的治疗剂。
• Pyrrolidine derivatives
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0289911A2

  公开（公告）日：1988-11-09

  A compound of the formula : wherein     R¹ is hydrogen or an acyl group,     R² is an acyl group,     R³ is carboxy(lower)alkyl, lower alkyl substituted with carboxy and one or more halogen atom(s), protected carboxy(lower)alkyl, carboxyaryl, protected carboxyaryl, carboxy, protected carboxy, hydroxy(lower)­alkyl, sulfino(lower)alkyl, phosphono(lower)alkyl, protected phosphono(lower)alkyl or halo(lower)­alkyl,     R⁷ is hydrogen or lower alkyl, and     A is (in which R⁸ is hydrogen or lower alkyl), and a pharmaceutically acceptable salt thereof, processes for its preparation and pharmaceutical compositions comprising them. The invention also relates to intermediates of the formula and process for production thereof.

  式中的化合物 其中 R¹ 是氢或酰基、 R² 是酰基 R³ 是羧基（低级）烷基、被羧基和一个或多个卤原子取代的低级烷基、受保护的羧基（低级）烷基、羧基芳基、受保护的羧基芳基、羧基、受保护的羧基、羟基（低级）烷基、亚磺酰基（低级）烷基、膦酰基（低级）烷基、受保护的膦酰基（低级）烷基或卤代（低级）烷基、 R⁷ 是氢或低级烷基，以及 A 是 (其中 R⁸ 是氢或低级烷基）、 及其药学上可接受的盐、制备工艺和包含它们的药物组合物。本发明还涉及式 及其生产工艺。
• US4916152A
  申请人：——

  公开号：US4916152A

  公开（公告）日：1990-04-10
• Synthesis and Biological Activity of 1-Phenylsulfonyl-4-Phenylsulfonylaminopyrrolidine Derivatives as Thromboxane A 2 Receptor Antagonists
  作者：Hiroshi Marusawa、Hiroyuki Setoi、Akihiko Sawada、Akio Kuroda、Jiro Seki、Yukio Motoyama、Hirokazu Tanaka

  DOI：10.1016/s0968-0896(01)00397-2

  日期：2002.5

  The synthesis and biological activity of novel 1-phenylsulfonyl-4- phenylsulfonylaminopyrrolidine analogues are described. All compounds were produced through modification of the substituent formally corresponding to the 1,3-dioxane ring system and the omega-octenol side chain of thromboxane A(2) (TXA(2)), in reference to the structure of Daltroban. Several compounds were found to be potent TXA(2) receptor antagonists. Compound 51a was the most effective inhibitor of 9.11-epoxymethano PGH(2) (U-46619)-induced rat aortic strip contraction (IC50 = 0.48 nM). (C) 2002 Elsevier Science Ltd. All rights reserved.