2-(2-(2-phenylthiazol-4-yl)ethyl)isoindoline-1,3-dione | 250258-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(2-(2-phenylthiazol-4-yl)ethyl)isoindoline-1,3-dione
• 英文别名: N-[2-(2-phenyl-thiazol-4-yl)-ethyl]-phthalimide；N-[2-(2-Phenyl-thiazol-4-yl)-aethyl]-phthalimid；2-[2-(2-phenyl-1,3-thiazol-4-yl)ethyl]-1H-isoindole-1,3(2H)-dione；2-[2-(2-phenyl-1,3-thiazol-4-yl)ethyl]isoindole-1,3-dione
• CAS: 250258-57-2
• 化学式: C₁₉H₁₄N₂O₂S
• 分子量: 334.398
• InChiKey: BDHKGZANHRLRPV-UHFFFAOYSA-N

物化性质

• 沸点：
  532.5±52.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-(2-phenylthiazol-4-yl)ethyl)isoindoline-1,3-dione 在 肼 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 4-(2-aminoethyl)-2-phenylthiazole
  参考文献：
  名称：

  组胺H1受体配体。第一部分：新型的噻唑-4-乙胺胺衍生物：合成和体外药理学。

  摘要：

  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）。

  DOI：

  10.1016/s0014-827x(99)00060-9
• 作为产物：
  描述：

  邻苯二甲酸亚胺 在 盐酸 、 溴 、 sodium hydroxide 作用下， 以 甲醇 、 乙酸乙酯 、 异丙醇 为溶剂， 生成 2-(2-(2-phenylthiazol-4-yl)ethyl)isoindoline-1,3-dione
  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

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）。
• USE OF ADAM9 INHIBITOR AS IMMUNOMODULATOR
  申请人：China Medical University

  公开号：EP3960171A1

  公开（公告）日：2022-03-02

  A use of an ADAM9 inhibitor in preparing an immunomodulator. The immunomodulator can change the distribution of immune cells in a tumor and increase the infiltration of the immune cells, thereby increasing the efficacy of cancer immunotherapy.

  一种 ADAM9 抑制剂在制备免疫调节剂中的用途。这种免疫调节剂可以改变肿瘤中免疫细胞的分布，增加免疫细胞的浸润，从而提高癌症免疫疗法的疗效。
• Composition including ADAM9 inhibitor and the use thereof
  申请人：China Medical University

  公开号：US11357759B2

  公开（公告）日：2022-06-14

  The present disclosure relates to an ADAM9 inhibitor compound of formula (I), including salts, hydrates and stereoisomers thereof, compositions thereof, and methods of use therefor, including treating a person in need thereof with an effective amount of the compound or composition, and detecting a resultant improvement in the person's health or condition.

  本公开涉及一种式（I）的ADAM9抑制剂化合物，包括其盐类、水合物和立体异构体，其组合物及其使用方法，包括用有效量的化合物或组合物治疗有需要的人，并检测该人的健康或状况因此得到的改善。
• THE SYNTHESIS OF THIAZOLE AMINES POSSESSING PHARMACOLOGICAL INTEREST. IV
  作者：W. S. Hinegardner、Treat B. Johnson

  DOI：10.1021/ja01372a047

  日期：1930.9
• Thiazole substituted by a primary alkylamino group
  申请人：WINTHROP CHEM CO INC

  公开号：US02020650A1

  公开（公告）日：1935-11-12