3-(1H-benzimidazol-1-ylmethyl)aniline | 562803-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 3-(1H-benzimidazol-1-ylmethyl)aniline
• 英文别名: 3-(1H-1,3-Benzodiazol-1-ylmethyl)aniline；3-(benzimidazol-1-ylmethyl)aniline
• CAS: 562803-83-2
• 化学式: C₁₄H₁₃N₃
• mdl: MFCD09812505
• 分子量: 223.277
• InChiKey: PBCMAQMJRXLGTE-UHFFFAOYSA-N

物化性质

• 沸点：
  461.8±47.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1H-benzimidazol-1-ylmethyl)aniline 在 四(三苯基膦)钯 N,N-二异丙基乙胺 作用下， 以 乙二醇二甲醚 、 异丙醇 为溶剂， 反应 120.5h， 生成 (3-(benzimidazol-1-ylmethyl)phenyl)(6-(2-methoxyphenyl)pyrimidin-4-yl)amine
  参考文献：
  名称：

  4-PHENYLAMINO-PYRIMIDINE DERIVATIVES HAVING PROTEIN KINASE INHIBITOR ACTIVITY

  摘要：

  本发明涉及通式（I）的化合物及其药用盐和溶剂化物，其中R1为卤素，乙烯基芳基，取代芳基，杂芳基或苯并[1,3]二噁唑基团，W为式—NH—SO2—R2或杂芳基或NHR3基团，其中R3为氢或杂芳基；n为1、2、3或4。此外，本发明还涉及含有至少一种通式（I）的化合物和/或其药用盐或溶剂化物的药物组合物，以及将它们用于制备用于预防和/或治疗蛋白激酶相关疾病，特别是CDK9相关疾病（例如细胞增殖性疾病、传染病、疼痛、心血管疾病和炎症）的药物组合物。

  公开号：

  US20120258968A1
• 作为产物：
  描述：

  3-硝基溴苄 在 potassium carbonate 、 tin(ll) chloride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 3-(1H-benzimidazol-1-ylmethyl)aniline
  参考文献：
  名称：

  A structure–Permeability study of small drug-like molecules

  摘要：

  A systematic structure permeability relationship study on a set of small drug-like molecules with log D values in the range -2.5 to 3 and carrying a diverse Arran of functionality reveals that the compounds with log D>0 and <3 are highly permeable. Surprisingly. several tetrazole derivatives were found to be substrates for efflux pump(s). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01035-1

文献信息

• [EN] 4-PHENYLAMINO-PYRIMIDINE DERIVATIVES HAVING PROTEIN KINASE INHIBITOR ACTIVITY<br/>[FR] DÉRIVÉS DE 4-PHÉNYLAMINO-PYRIMIDINE AYANT UNE ACTIVITÉ D'INHIBITION D'UNE PROTÉINE KINASE
  申请人：VICHEM CHEMIE KUTATO KFT

  公开号：WO2011077171A1

  公开（公告）日：2011-06-30

  The invention relates compounds of general formula (I) and pharmaceutically acceptable salts and solvates thereof wherein R1 is halogen, vinylene-aryl, substituted aryl, heteroaryl or a benzo[1,3]dioxolil group, W is a group of formula -NH-SO2-R2 or heteroaryl group or NHR3 group where R3 is hydrogen or heteroaryl; and n is 1, 2, 3 or 4. Furthermore, the present invention is directed to pharmaceutical composition containing at least one compound of general formula (I) and/or pharmaceutically acceptable salts or solvates thereof and for the use of them for the preparation of pharmaceutical compositions for the prophylaxis and/or the treatment of protein kinase related, especially CDK9-related diseases e.g. cell proliferative disease, infectious disease, pain, cardiovascular disease and inflammation.

  该发明涉及一般式（I）的化合物及其药用可接受的盐和溶剂化合物，其中R1为卤素、乙烯基芳基、取代芳基、杂芳基或苯并[1,3]二噁唑基团，W为式-NH-SO2-R2或杂芳基或NHR3基团，其中R3为氢或杂芳基；n为1、2、3或4。此外，本发明涉及一种含有至少一种一般式（I）的化合物和/或其药用可接受的盐或溶剂化合物的药物组合物，并用于制备用于预防和/或治疗蛋白激酶相关疾病，特别是CDK9相关疾病，如细胞增殖性疾病、传染病、疼痛、心血管疾病和炎症的药物组合物。
• Novel compounds with potent CDK9 inhibitory activity for the treatment of myeloma
  作者：Zsófia Czudor、Mária Balogh、Péter Bánhegyi、Sándor Boros、Nóra Breza、Judit Dobos、Márk Fábián、Zoltán Horváth、Eszter Illyés、Péter Markó、Anna Sipos、Csaba Szántai-Kis、Bálint Szokol、László Őrfi

  DOI：10.1016/j.bmcl.2018.01.002

  日期：2018.2

  Cyclin-dependent kinases (CDKs) and Polo-like kinases (PLKs) play key role in the regulation of the cell cycle. The aim of our study was originally the further development of our recently discovered polo-like kinase 1 (PLK1) inhibitors. A series of new 2,4-disubstituted pyrimidine derivatives were synthesized around the original hit, but their PLK1 inhibitory activity was very poor. However the novel compounds showed nanomolar CDK9 inhibitory activity and very good antiproliferative effect on multiple myeloma cell lines (RPMI-8226). (C) 2018 Elsevier Ltd. All rights reserved.
• US9040529B2
  申请人：——

  公开号：US9040529B2

  公开（公告）日：2015-05-26
• 10.1038/s41419-024-06724-4
  作者：Valdez Capuccino、Kleitke、Szokol、Svajda、Martin、Bonechi、Krekó、Azami、Montinaro、Wang、Nikolov、Kaiser、Bonasera、Saggau、Scholz、Schmitt、Beleggia、Reinhardt、George、Liccardi、Walczak、Tóvári、Brägelmann、Montero、Sos、Őrfi、Peltzer

  DOI：10.1038/s41419-024-06724-4

  日期：——
• A structure–Permeability study of small drug-like molecules
  作者：Thomas Fichert、Mehran Yazdanian、John R. Proudfoot

  DOI：10.1016/s0960-894x(02)01035-1

  日期：2003.2

  A systematic structure permeability relationship study on a set of small drug-like molecules with log D values in the range -2.5 to 3 and carrying a diverse Arran of functionality reveals that the compounds with log D>0 and <3 are highly permeable. Surprisingly. several tetrazole derivatives were found to be substrates for efflux pump(s). (C) 2003 Elsevier Science Ltd. All rights reserved.