4-氯甲基-2-(4-硝基苯基)-噻唑 | 4771-32-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氯甲基-2-(4-硝基苯基)-噻唑
• 英文名称: 4-chloromethyl-2-(4-nitrophenyl)-thiazole
• 英文别名: 4-Chlormethyl-2-(4-nitro-phenyl)-thiazol；4-(Chloromethyl)-2-(4-nitrophenyl)-1,3-thiazole
• CAS: 4771-32-8
• 化学式: C₁₀H₇ClN₂O₂S
• mdl: MFCD05860576
• 分子量: 254.697
• InChiKey: LFVAPAHRHVOVHQ-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  435.1±55.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-氯甲基-2-(4-硝基苯基)-噻唑 在 sodium dichromate 、 水 、 溴 作用下， 以 溶剂黄146 为溶剂， 反应 2.5h， 生成 5-bromo-2-(4-nitro-phenyl)-thiazole-4-carbaldehyde
  参考文献：
  名称：

  Sommelet 反应在 2-Aryl-4-chloromethyl-5-bromothiazoles 中的应用对一些杂环类化合物的研究 XXXI

  摘要：

  描述了 2-芳基-4-氯甲基-5-溴噻唑在直接和间接 Sommelet 反应条件下的行为。

  DOI：

  10.1002/ardp.19743070202
• 作为产物：
  描述：

  对硝基苯甲腈 在 tetraphosphorus decasulfide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 6.5h， 生成 4-氯甲基-2-(4-硝基苯基)-噻唑
  参考文献：
  名称：

  Agonists for the Adenosine A₁ Receptor with Tunable Residence Time. A Case for Nonribose 4-Amino-6-aryl-5-cyano-2-thiopyrimidines

  摘要：

  We report the synthesis and evaluation of previously unreported 4-amino-6-aryl-5-cyano-2-thiopyrimidines as selective human adenosine A(1) receptor (hA(1)AR) agonists with tunable binding kinetics, this without affecting their nanomolar affinity for the target receptor. They show a very diverse range of kinetic profiles (from 1 min (compound 52) to 1 h (compound 43)), and their structure-affinity relationships (SAR) and structure-kinetics relationships (SKR) were established. When put in perspective with the increasing importance of binding kinetics in drug discovery, these results bring new evidence of the consequences of affinity-only driven selection of drug candidates, that is, the potential elimination of slightly less active compounds that may display preferable binding kinetics.

  DOI：

  10.1021/jm401643m

文献信息

• Simiti,I.; Farkas,M., Chemische Berichte, 1965, vol. 98, p. 3446 - 3450
  作者：Simiti,I.、Farkas,M.

  DOI：——

  日期：——
• Fridman, Zhurnal Obshchei Khimii, 1954, vol. 24, p. 909,910, 915; engl. Ausg. S. 909, 910, 912
  作者：Fridman

  DOI：——

  日期：——
• SILBERG, S., REV. ROUM. CHIM., 1983, 28, N 6, 645-651
  作者：SILBERG, S.

  DOI：——

  日期：——
• SIMITI I.; FARKAS M., ACTA CHIM. ACAD. SCI. HUNG. <ACAS-A2>, 1974, 83, NO 3-4, 381-389
  作者：SIMITI I.、 FARKAS M.

  DOI：——

  日期：——
• Agonists for the Adenosine A₁ Receptor with Tunable Residence Time. A Case for Nonribose 4-Amino-6-aryl-5-cyano-2-thiopyrimidines
  作者：Julien Louvel、Dong Guo、Marta Agliardi、Tamara A. M. Mocking、Roland Kars、Tan Phát Pham、Lizi Xia、Henk de Vries、Johannes Brussee、Laura H. Heitman、Adriaan P. IJzerman

  DOI：10.1021/jm401643m

  日期：2014.4.24

  We report the synthesis and evaluation of previously unreported 4-amino-6-aryl-5-cyano-2-thiopyrimidines as selective human adenosine A(1) receptor (hA(1)AR) agonists with tunable binding kinetics, this without affecting their nanomolar affinity for the target receptor. They show a very diverse range of kinetic profiles (from 1 min (compound 52) to 1 h (compound 43)), and their structure-affinity relationships (SAR) and structure-kinetics relationships (SKR) were established. When put in perspective with the increasing importance of binding kinetics in drug discovery, these results bring new evidence of the consequences of affinity-only driven selection of drug candidates, that is, the potential elimination of slightly less active compounds that may display preferable binding kinetics.