1,1-dimethylethyl N-(3-(thioureidomethyl)phenylmethyl)carbamate | 163490-94-6

• 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: 1,1-dimethylethyl N-(3-(thioureidomethyl)phenylmethyl)carbamate
• 英文别名: Tert-butyl N-(3-((thioureido)methyl)benzyl)carbamate；tert-butyl N-[[3-[(carbamothioylamino)methyl]phenyl]methyl]carbamate
• CAS: 163490-94-6
• 化学式: C₁₄H₂₁N₃O₂S
• 分子量: 295.406
• InChiKey: LWIISHWUAOAMOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl N-(3-(thioureidomethyl)phenylmethyl)carbamate 、 碘甲烷 在 盐酸 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 以46%的产率得到1-(3-(Aminomethyl)benzyl)-S-methylisothiourea
  参考文献：
  名称：

  Substituted urea and isothiourea derivatives as no synthase inhibitors

  摘要：

  N-取代脲衍生物用于制造治疗存在抑制NO合酶酶优势的疾病的药物，特别是脑缺血，以及相关的药物配方已被披露。还描述了新颖的N-取代脲衍生物及其制备方法。

  公开号：

  US06090846A1
• 作为产物：
  描述：

  N-[3-(氨基甲基)苄基]氨基甲酸叔丁酯 在 氨 、 calcium carbonate 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 19.5h， 生成 1,1-dimethylethyl N-(3-(thioureidomethyl)phenylmethyl)carbamate
  参考文献：
  名称：

  Synthesis of N-benzyl- and N-phenyl-2-amino-4,5-dihydrothiazoles and thioureas and evaluation as modulators of the isoforms of nitric oxide synthase

  摘要：

  Inhibition of the isoforms of nitric oxide synthase (NOS) has important applications in therapy of several diseases, including cancer. Using 1400W [N-(3-aminomethylbenzyl)acetamidme], thiocitrulline and N-delta-(4,5-dihydrothiazol-2-yl)ornithine as lead compounds, series of N-benzyl- and N-phenyl-2-amino-4,5-dihydrothiazoles and thioureas were designed as inhibitors of NOS. Ring-substituted benzyl and phenyl isothiocyanates were synthesised by condensation of the corresponding amines with thiophosgene and addition of ammonia gave the corresponding thioureas in high yields. The substituted 2-amino-4,5-dihydrothiazoles were approached by two routes. Treatment of simple benzylamines with 2-methylthio-4,5-dihydrothiazole at 180degreesC afforded the corresponding 2-benzylamino-4,5-dihydrothiazoles. For less nucleophilic amines and those carrying more thermally labile substituents, the 4,5-dihydrothiazoles were approached by acid-catalysed cyclisation of N-(2-hydroxyethyl)thioureas. This cyclisation was shown to proceed by an S(N)2-like process. Modest inhibitory activity was shown by most of the thioureas and 4,5-dihydrothiazoles, with N-(3-aminomethylphenyl)thiourea (IC50 = 13 muM vs rat neuronal NOS and IC50 = 23 muM vs rat inducible NOS) and 2-(3-aminomethylphenylamino)-4,5-dihydrothiazole (IC50 - 13 muM vs rat neuronal NOS and IC50 = 19 muM vs human inducible NOS) being the most potent. Several thioureas and 4,5-dihydrothiazoles were found to stimulate the activity of human inducible NOS in a time-dependent manner. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00451-6

文献信息

• SUBSTITUTED UREA AND ISOTHIOUREA DERIVATIVES AS NO SYNTHASE INHIBITORS
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0723438A1

  公开（公告）日：1996-07-31
• US6090846A
  申请人：——

  公开号：US6090846A

  公开（公告）日：2000-07-18
• US6225305B1
  申请人：——

  公开号：US6225305B1

  公开（公告）日：2001-05-01
• US6297276B1
  申请人：——

  公开号：US6297276B1

  公开（公告）日：2001-10-02
• [EN] SUBSTITUTED UREA AND ISOTHIOUREA DERIVATIVES AS NO SYNTHASE INHIBITORS<br/>[FR] DERIVES SUBSTITUES DE L'UREE ET DE L'ISOTHIOUREE UTILISES COMME INHIBITEURS DE L'OXYDE NITRIQUE SYNTHASE
  申请人：——

  公开号：WO1995009619A2

  公开（公告）日：1995-04-13

  [EN] The use of an N-substituted urea derivative for the manufacture of a medicament for the treatment of a condition where there is an advantage in inhibiting the NO synthase enzyme, in particular cerebral ischemia, and pharmaceutical formulations therefor are disclosed. Novel N-substituted urea derivatives and processes for the preparation thereof are also described.
  [FR] L'invention se rapporte à l'utilisation d'un dérivé de l'urée N-substitué dans la fabrication d'un médicament destiné au traitement d'une affection, en particulier de l'ischémie cérébrale, dans laquelle il y a un avantage à inhiber l'oxyde nitrique synthase; l'invention concerne également les formulations pharmaceutiques de ce dérivé, ainsi que des nouveaux dérivés de l'urée N-substitués et leurs procédés de préparation.