benzo[1,3]dioxol-5-ylmethyl-{3-[(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-propyl-amino]-propyl}-carbamic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: benzo[1,3]dioxol-5-ylmethyl-{3-[(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-propyl-amino]-propyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-(1,3-benzodioxol-5-ylmethyl)-N-[3-[(3-imidazol-1-yl-1,2,4-thiadiazol-5-yl)-propylamino]propyl]carbamate
• 化学式: C₂₄H₃₂N₆O₄S
• 分子量: 500.622
• InChiKey: FBHAYBGGAXGFLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzo[1,3]dioxol-5-ylmethyl-{3-[(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-propyl-amino]-propyl}-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 N'-benzo[1,3]dioxol-5-ylmethyl-N-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-N-propyl-propane-1,3-diamine
  参考文献：
  名称：

  Identification and SAR of selective inducible nitric oxide synthase (iNOS) dimerization inhibitors

  摘要：

  We have identified and synthesized a series of imidazole containing dimerization inhibitors of inducible nitric oxide synthase (iNOS). The necessity of key imidazole and piperonyl functionality was demonstrated and SAR studies led to the identification of compound 35, which showed a dose dependant inhibition in multiple pain models, including tactile allodynia induced by spinal nerve ligation (Chung model). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.112
• 作为产物：
  描述：

  benzo[1,3]dioxol-5-yl-methyl-(3-bromo-propyl)-carbamic acid tert-butyl ester 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成 benzo[1,3]dioxol-5-ylmethyl-{3-[(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-propyl-amino]-propyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Identification and SAR of selective inducible nitric oxide synthase (iNOS) dimerization inhibitors

  摘要：

  We have identified and synthesized a series of imidazole containing dimerization inhibitors of inducible nitric oxide synthase (iNOS). The necessity of key imidazole and piperonyl functionality was demonstrated and SAR studies led to the identification of compound 35, which showed a dose dependant inhibition in multiple pain models, including tactile allodynia induced by spinal nerve ligation (Chung model). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.112

文献信息

• NOVEL METHOD OF PREPARATION OF 5-CHLORO-3-IMIDAZOL-1-YL-[1,2,4]THIADIAZOLE AND (3-IMIDAZOL-1-YL-[1,2,4]THIADIAZOL-5YL)-DIALKYL-AMINES
  申请人：Herbert R. Mark

  公开号：US20070123572A1

  公开（公告）日：2007-05-31

  The present invention discloses a novel method for preparing 3-imidazol-1-yl-[1,2,4]thiadiazole derivatives, particularly to a method of preparing 5-halo-3-imidazol-1-yl-[1,2,4]thiadiazole, more particularly (3 -imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-dialkyl-amines, that afford a high yield of pure product.

  本发明公开了一种制备3-咪唑-1-基-[1,2,4]噻二唑衍生物的新方法，特别是一种制备5-卤代-3-咪唑-1-基-[1,2,4]噻二唑的方法，更具体地说是（3-咪唑-1-基-[1,2,4]噻唑-5-基）-二烷基胺的制备方法，该方法提供了高产率的纯产品。
• INDUCIBLE NITRIC OXIDE SYNTHASE DIMERIZATION INHIBITORS
  申请人：Kalypsys, Inc.

  公开号：EP1817030A2

  公开（公告）日：2007-08-15
• US7825256B2
  申请人：——

  公开号：US7825256B2

  公开（公告）日：2010-11-02
• [EN] INDUCIBLE NITRIC OXIDE SYNTHASE DIMERIZATION INHIBITORS<br/>[FR] INHIBITEURS DE LA DIMERISATION DE L'OXYDE NITRIQUE SYNTHASE INDUCTIBLE
  申请人：KALYPSYS INC

  公开号：WO2006060424A2

  公开（公告）日：2006-06-08

  [EN] The present invention relates to compounds and methods useful as inhibitors of nitric oxide synthase. Certain compounds of the subject invention have the following structural formula:(I) wherein T, X, and Y are independently selected from the group consisting of CR⁴, N, NW, S, and O; U is selected from the group consisting of CR¹⁰ and N; V is selected from the group consisting of CR⁴ and N; W and Ware independently selected from the group consisting of _CH2, CR⁷R⁸, NR⁹, O, N(O), S(O)_q and C(O); n, m and p are independently an integer from 0 to 5; q is 0, 1, or 2; and other substituents are as defined herein. Other compounds of the subject invention have structural formulas as defined herein. Also disclosed herein are pharmaceutical compositions comprising the compounds of the subject invention.
  [FR] L'invention concerne des composés et des méthodes utiles comme inhibiteurs de l'oxyde nitrique synthase. Certains composés selon l'invention comprennent la formule structurelle suivante : (I) dans laquelle T, X et Y sont choisis indépendamment dans le groupe constitué de CR⁴, N, NW, S et O ; U est choisi dans le groupe constitué de CR¹⁰ et N ; V est choisi dans le groupe constitué de CR⁴ et N; W et W' sont indépendamment choisi dans le groupe constitué de CH_2, CR⁷R⁸, NR⁹, O, N(O), S(O)_q et C(O) ; n, m et p valent indépendamment un entier de 0 à 5 ; q vaut 0, 1 ou 2 ; et d'autres substituants sont tels que définis dans le descriptif. D'autres composés selon l'invention présentent des formules structurelles telles que définies dans le descriptif. L'invention concerne également des compositions pharmaceutiques comprenant les composés selon l'invention.
• Identification and SAR of selective inducible nitric oxide synthase (iNOS) dimerization inhibitors
  作者：Timothy C. Gahman、Mark R. Herbert、Henk Lang、Angie Thayer、Kent T. Symons、Phan Manh Nguyen、Mark E. Massari、Sara Dozier、Yan Zhang、Marciano Sablad、Tadimeti S. Rao、Stewart A. Noble、Andrew K. Shiau、Christian A. Hassig

  DOI：10.1016/j.bmcl.2011.08.112

  日期：2011.11

  We have identified and synthesized a series of imidazole containing dimerization inhibitors of inducible nitric oxide synthase (iNOS). The necessity of key imidazole and piperonyl functionality was demonstrated and SAR studies led to the identification of compound 35, which showed a dose dependant inhibition in multiple pain models, including tactile allodynia induced by spinal nerve ligation (Chung model). (C) 2011 Elsevier Ltd. All rights reserved.