4-(2-aminoethyl)-2-phenylthiazole | 645393-01-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(2-aminoethyl)-2-phenylthiazole
• 英文别名: 2-(2-Phenyl-thiazol-4-yl)-ethylamine；2-(2-phenyl-1,3-thiazol-4-yl)ethanamine
• CAS: 645393-01-7
• 化学式: C₁₁H₁₂N₂S
• mdl: MFCD08449273
• 分子量: 204.296
• InChiKey: CISTXXCPQIZSIS-UHFFFAOYSA-N

物化性质

• 沸点：
  362.9±34.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  3-糠酸 、 4-(2-aminoethyl)-2-phenylthiazole 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 N-(2-(2-phenylthiazol-4-yl)ethyl)furan-3-carboxamide
  参考文献：
  名称：

  Hit-to-Lead Optimization of a Novel Class of Potent, Broad-Spectrum Trypanosomacides

  摘要：

  The parasitic trypanosomes Trypanosoma brucei and T. cruzi are responsible for significant human suffering in the form of human African trypanosomiasis (HAT) and Chagas disease. Drugs currently available to treat these neglected diseases leave much to be desired. Herein we report optimization of a novel class of N-(2-(2-phenylthiazol-4-yl)ethyl)amides, carbamates, and ureas, which rapidly, selectively, and potently kill both species of trypanosome. The mode of action of these compounds is unknown but does not involve CYP51 inhibition. They do, however, exhibit clear structure activity relationships, consistent across both trypanosome species. Favorable physicochemical parameters place the best compounds in CNS drug-like chemical space but, as a class, they exhibit poor metabolic stability. One of the best compounds (64a) cleared all signs of T. cruzi infection in mice when CYP metabolism was inhibited, with sterile cure achieved in one mouse. This family of compounds thus shows significant promise for trypanosomiasis drug discovery.

  DOI：

  10.1021/acs.jmedchem.6b00442
• 作为产物：
  描述：

  4-(2-Chlorethyl)-2-phenyl-thiazol 在 氨 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 4-(2-aminoethyl)-2-phenylthiazole
  参考文献：
  名称：

  Palazzo,G.; Tavella,M., Gazzetta Chimica Italiana, 1962, vol. 92, p. 1084 - 1092

  摘要：

  DOI：

文献信息

• Histamine H1 receptor ligands
  作者：K. Walczyński、H. Timmerman、O.P. Zuiderveld、M.Q. Zhang、R. Glinka

  DOI：10.1016/s0014-827x(99)00060-9

  日期：1999.8

  A series of 2-substituted thiazol-4-ylethanamines have been synthesized and tested for their histaminergic H1-receptor activities. The compounds with 2-phenyl substitution, regardless of the different physicochemical properties of the meta-substituents at the phenyl ring, showed weak H1-agonistic activity with pD2 values ranging from 4.35 to 5.36. When the phenyl group was replaced by a benzyl group

  已经合成了一系列2-取代的噻唑-4-吡啶胺，并测试了它们的组胺能H1-受体活性。具有2-苯基取代基的化合物，无论苯环上间位取代基的理化性质如何不同，均表现出较弱的H1激动活性，pD2值为4.35至5.36。当苯基被苄基取代时，所得化合物均表现出弱的H1-拮抗活性（pA2：4.14-4.82）。
• Synthesis and evaluation of novel 2,4-disubstituted arylthiazoles against <i>T. brucei</i>
  作者：Markos-Orestis Georgiadis、Violeta Kourbeli、Ioannis P. Papanastasiou、Andrew Tsotinis、Martin C. Taylor、John M. Kelly

  DOI：10.1039/c9md00478e

  日期：——

  The design, synthesis and pharmacological evaluation of the 4-substituted-2-[3-(adamant-1-yl)-4-fluorophenyl]thiazoles 1a–j, the 4-substituted-2-[4-(adamant-1-yl)phenyl]thiazoles 2a–h, the 2-substituted-4-[4-(adamant-1-yl)phenyl]thiazoles 3a–e, the N-substituted 2-phenylthiazol-4-ethylamides 4a, b and the N-substituted 4-phenylthiazol-2-ethylamides 4c, d is described. Compounds 1a and 2a exhibit trypanocidal

  4-取代-2-[3-(adamant-1-yl)-4-氟苯基]噻唑1a-j、4-取代-2-[4-(adamant-1- )的设计、合成和药理学评价基）苯基]噻唑2a-h，2-取代的-4-[4-（金刚烷-1-基）苯基]噻唑3a-e，N-取代的 2-苯基噻唑-4-乙基酰胺4a，b和N描述了-取代的4-苯基噻唑-2-乙基酰胺4c、d。化合物1a和2a在 IC 50 = 0.42 μM 和 IC 50范围内表现出杀锥虫活性= 0.80 μM，分别。这两种衍生物都带有亲脂性末端，由 4-(1-金刚烷基) 苯基或 3-(1-金刚烷基) 苯基部分、1,3-噻唑环和由烷基胺组成的官能末端组成并且可以被认为是治疗布氏锥虫感染的有希望的候选者。
• [EN] HETEROCYCLIC COMPOUNDS AND USE OF SAME<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEUR UTILISATION
  申请人：UNIV MONASH

  公开号：WO2015172196A1

  公开（公告）日：2015-11-19

  Novel heterocyclic compounds are provided which display useful efficacy in the treatment of diseases caused by trypanosomatids. Particularly, the compounds of the invention are useful in the treatment of HAT and/or Chagas disease and/or Animal African trypanosomiasis (AAT).

  提供了新型杂环化合物，这些化合物在治疗由锥虫引起的疾病中显示出有效性。特别是，本发明的化合物在治疗HAT和/或Chagas病和/或动物非洲锥虫病（AAT）方面具有用途。
• PDE10 MODULATORS
  申请人：Bachmann Stephan

  公开号：US20130059833A1

  公开（公告）日：2013-03-07

  The present invention relates to compounds of formula (I) wherein R 1 , R 2 , R 3 , R 5 , W, X, X 1 , Y, Y 1 , Z and Z 1 are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds inhibit PDE10A and can be used in the treatment of CNS disorders such as schizophrenia, Alzheimer's disease, and Parkinson's disease.

  本发明涉及式(I)的化合物，其中R1、R2、R3、R5、W、X、X1、Y、Y1、Z和Z1如描述和权利要求中定义，并且其生理上可接受的盐。这些化合物抑制PDE10A，可用于治疗中枢神经系统疾病，如精神分裂症、阿尔茨海默病和帕金森病。
• [EN] PDE10 MODULATORS<br/>[FR] MODULATEURS DE PDE10
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013034506A1

  公开（公告）日：2013-03-14

  The present invention relates to compounds of formula (I) wherein R1, R2, R3, R5, W, X, X1, Y, Y1, Z and Z1 are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds inhibit PDE10A and can be used as medicaments.

  本发明涉及以下式（I）的化合物，其中R1、R2、R3、R5、W、X、X1、Y、Y1、Z和Z1如描述和权利要求中所定义，并且其生理学上可接受的盐。这些化合物抑制PDE10A，可用作药物。