1,1-dimethylethyl N-(3-thioureidophenylmethyl)carbamate | 180079-71-4

• 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-thioureidophenylmethyl)carbamate
• 英文别名: N-(3-thioureidophenylmethyl)carbamic acid t-butyl ester；N-(3-(t-butoxycarbonylaminomethyl)phenyl)thiourea；(3-thioureido-benzyl)-carbamic acid tert-butyl ester；tert-butyl N-[[3-(carbamothioylamino)phenyl]methyl]carbamate
• CAS: 180079-71-4
• 化学式: C₁₃H₁₉N₃O₂S
• 分子量: 281.379
• InChiKey: ACWLLXLYCXMXDQ-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200 °C
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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-thioureidophenylmethyl)carbamate 、 碘乙烷 以the same procedure of Example 4 gave 178 mg of the titled compound (yield, 68%)的产率得到N-(3-(S-ethylisothioureido)phenylmethyl)carbamic acid t-butyl ester hydroiodide
  参考文献：
  名称：

  Aniline derivatives possessing an inhibitory effect of nitric oxide synthase

  摘要：

  化合物的一般式表示为（1）：（其中R1是SR6或NR7R8，其中R6通常是具有1-6个碳原子的烷基基团，R7是氢原子，具有1-6个碳原子的烷基基团或硝基基团，R8是氢原子或具有1-6个碳原子的烷基基团；R2和R3通常是氢原子或具有1-6个碳原子的烷基基团；R4是氢原子，具有1-6个碳原子的烷基基团或酰胺基团，其胺部分可以被烷基或硝基基团取代；R5是氢原子或具有1-6个碳原子的烷基基团；Y1、Y2、Y3和Y4可以相同也可以不同，通常是氢原子、卤原子或具有1-6个碳原子的烷氧基团；n和m均为0或1的整数），或这些化合物的可能立体异构体或光学活性形式，或其药学上可接受的盐。这些化合物具有强效的一氧化氮合酶抑制活性，并可用作脑血管疾病的治疗药物。

  公开号：

  US06534546B1
• 作为产物：
  描述：

  3-硝基苄胺 在 氨 、 三乙胺 、 calcium carbonate 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 38.0h， 生成 1,1-dimethylethyl N-(3-thioureidophenylmethyl)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

• Thiazole derivatives
  申请人：Neidhart Werner

  公开号：US20050038089A1

  公开（公告）日：2005-02-17

  Thiazole derivatives of formula I are provided as well as pharmaceutically acceptable salts and esters thereof, wherein R 1 to R 5 , a and b have the significance given in the specification. The compounds are neuropeptide Y Y5 receptor antagonists which can be used for the treatment of obesity.

  提供了式I的噻唑衍生物，以及其药用盐和酯，其中R1至R5，a和b的含义如规范中所述。这些化合物是神经肽Y Y5受体拮抗剂，可用于治疗肥胖。
• Aromatic amine derivatives having NOS inhibiting action
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US06331553B1

  公开（公告）日：2001-12-18

  Compounds represented by the general formula (1): (where R1 and R2 are typically a hydrogen atom; R3 and R4 are typically a hydrogen atom or a lower alkyl group; R5 is typically a hydrogen atom; X1, X2, X3 and X4 are typically a hydrogen atom or a lower alkoxy group; A is typically an optionally substituted pyridine ring; m and n are each 0 or 1) have an NOS inhibiting activity and are useful as therapeutics of cerebrovascular diseases and other pharmaceuticals.

  通式（1）代表的化合物：（其中R1和R2通常是氢原子；R3和R4通常是氢原子或较低的烷基基团；R5通常是氢原子；X1、X2、X3和X4通常是氢原子或较低的烷氧基团；A通常是一个可选取代的吡啶环；m和n各自为0或1）具有NOS抑制活性，并可用作脑血管疾病和其他药物的治疗药物。
• AROMATIC AMINE DERIVATIVES HAVING NOS INHIBITORY EFFECT
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP0949242A1

  公开（公告）日：1999-10-13

  Compounds represented by the general formula (1): (where R1 and R2 are typically a hydrogen atom; R3 and R4 are typically a hydrogen atom or a lower alkyl group; R5 is typically a hydrogen atom; X1, X2, X3 and X4 are typically a hydrogen atom or a lower alkoxy group; A is typically an optionally substituted pyridine ring; m and n are each 0 or 1) have an NOS inhibiting activity and are useful as therapeutics of cerebrovascular diseases and other pharmaceuticals.

  通式(1)所代表的化合物： (其中 R1 和 R2 通常为氢原子；R3 和 R4 通常为氢原子或低级烷基；R5 通常为氢原子；X1、X2、X3 和 X4 通常为氢原子或低级烷氧基；A 通常为任选取代的吡啶环；m 和 n 各为 0 或 1）具有 NOS 抑制活性，可用作脑血管疾病的治疗剂和其他药物。
• ANILINE DERIVATIVES HAVING NITROGEN MONOXIDE SYNTHASE INHIBITORY ACTIVITY
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP0798292B1

  公开（公告）日：2004-11-03
• 2-AMINO-5-BENZOYLTHIAZOLE NPY ANTAGONISTS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1658288A1

  公开（公告）日：2006-05-24