3-allyl-2-methyl-3H-benzimidazole-5-ylamine | 1434623-28-5

• 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-allyl-2-methyl-3H-benzimidazole-5-ylamine
• 英文别名: 3-allyl-2-methyl-3H-benzimidazol-5-ylamine；2-Methyl-3-prop-2-enylbenzimidazol-5-amine
• CAS: 1434623-28-5
• 化学式: C₁₁H₁₃N₃
• 分子量: 187.244
• InChiKey: WNZWKJLZTKFSLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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-allyl-2-methyl-3H-benzimidazole-5-ylamine 以 乙醇 、 异丙醇 为溶剂， 反应 72.0h， 生成 N-(3-allyl-2-methyl-3H-benzo[d]imidazol-5-yl)-2-morpholino-9H-purin-6-amine
  参考文献：
  名称：

  Purine-benzimidazole hybrids: Synthesis, single crystal determination and in vitro evaluation of antitumor activities

  摘要：

  In an effort to identify novel compounds for the treatment of cancer, a diverse array of potential bioactive hybrid, purine-benzimidazole was synthesized in good yields through nucleophilic substitution at C6 position of purine ring with versatile cyclic amines at C2 position. The structures of newly prepared compounds were confirmed by IR, H-1, C-13 NMR, mass spectroscopy and, in case of 19, by single crystal Xray diffraction analysis. The newly synthesized compounds were evaluated against 60 human tumour cell lines at one dose concentration level. Compound 6 exhibited significant growth inhibition and was evaluated as 60 cell panel at five dose concentration levels. Compound 6 proved to be 1.25 fold more active than the positive control 5-FU, with GI(50) value of 18.12 mu M (MG-MID). Interaction of the compounds with Aurora-A enzyme involved in the process of propagation of cancer, has also been investigated. Compound 6 showed selectivity towards Aurora-A kinase inhibition with IC50 value of 0.01 mu M. Molecular docking studies in the active binding site provided theoretical support for the experimental biological data acquired. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.036
• 作为产物：
  描述：

  2-甲基-5-硝基苯并咪唑 在 盐酸 、 tin(II) chloride dihdyrate 、 sodium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.0h， 生成 3-allyl-2-methyl-3H-benzimidazole-5-ylamine
  参考文献：
  名称：

  Synthesis, single crystal and antitumor activities of benzimidazole–quinazoline hybrids

  摘要：

  A series of novel regioisomeric hybrids of quinazoline/ benzimidazole viz. (3-allyl-2-methyl-3H-benzimidazol-5-yl)-(2-substituted-quinazolin-4-yl)-amine and (1-allyl-2-methyl-1H-benzimidazol-5-yl)(2-substituted-quinazolin-4-yl)-amine of biological interest were synthesized. All the synthesized compounds were well characterized by H-1 and C-13 NMR as well as mass spectroscopy. The newly synthesized compounds were screened for in vitro antitumor activities against 60 tumor cell lines panel assay. A significant inhibition for cancer cells were observed with compound 9 and also more active against known drug 5-fluorouracil (5-FU) in some tumor cell lines. Compound 9 displayed appreciable anticancer activity against leukemia, colon, melanoma, renal and breast cancer cell lines. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.107

文献信息

• [EN] INHIBITORS OF 11-BETA-HYDROXY STEROID DEHYDROGENASE TYPE 1 AND TYPE 2<br/>[FR] INHIBITEURS DE 11-BETA-HYDROXY STEROIDE DEHYDROGENASE DE TYPE 1 ET DE TYPE 2
  申请人：STERIX LTD

  公开号：WO2004037251A1

  公开（公告）日：2004-05-06

  There is provided a compound having Formula (I): wherein one of R1 and R2 is a group of the Formula (a), wherein R4 is selected from H and hydrocarbyl, R5 is a hydrocarbyl group and L is an optional linker group, or R1 and R2 together form a ring substituted with the group (Formula (a)) wherein R3 is H or a substituent, and wherein X is selected from S, O, NR6 and C(R7)(R8), wherein R6 is selected from H and hydrocarbyl groups, wherein each of R7 and R8 are independently selected from H and hydrocarbyl groups.

  提供一种具有化学式(I)的化合物：其中R1和R2中的一个是化学式(a)的基团，其中R4从H和烃基中选择，R5是烃基，L是可选的连接基团，或者R1和R2一起形成一个环，该环被基团(FORMULA (a))取代，其中R3是H或取代基，X从S、O、NR6和C(R7)(R8)中选择，其中R6从H和烃基中选择，R7和R8分别从H和烃基中独立选择。
• Compound
  申请人：——

  公开号：US20040143124A1

  公开（公告）日：2004-07-22

  A compound having Formula I 1 wherein one of R 1 and R 2 is a group of the formula 2 wherein R 4 is selected from H and hydrocarbyl, R 5 is a hydrocarbyl group and L is an optional linker group, or R 1 and R 2 together form a ring substituted with the group 3 wherein R 3 is H or a substituent, and wherein X is selected from S, O, NR 6 and C(R 7 )(R 8 ), wherein R 6 is selected from H and hydrocarbyl groups, wherein each of R 7 and R 8 are independently selected from H and hydrocarbyl groups.

  化合物具有I1式，其中R1和R2中的一个是公式2的基团，其中R4从H和烃基中选择，R5是烃基团，L是可选的连接基团，或者R1和R2一起形成带有基团3的环，其中R3是H或取代基，X从S，O，NR6和C（R7）（R8）中选择，其中R6从H和烃基团中选择，R7和R8各自独立地从H和烃基团中选择。
• Synthesis and in vitro antitumor evaluation of primary amine substituted quinazoline linked benzimidazole
  作者：Kamaldeep Paul、Alka Sharma、Vijay Luxami

  DOI：10.1016/j.bmcl.2013.12.005

  日期：2014.1

  By combining the structural features of quinazoline and benzimidazole, new hybrid regioisomeric molecules with substituted primary amines have been synthesized. Evaluation of these molecules over 60 cancer cell line panel has identified three molecules as most potent anticancer agents. Compound 10 showed ten and eleven folds more activity than respective quinazoline and benzimidazole class of compounds with GI(50) value of 1.64 mu M. Compound 11 (GI(50) value of 0.81 mu M) showed almost twenty and twenty-two fold more activity than quinazoline and benzimidazole analogue, respectively while compound 12 (GI(50) value of 4.52 mu M) has four fold more activity than quinazoline and benzimidazole analogue. In vitro evaluation of compound 11 exhibited remarkable anticancer activity towards colon cancer cell lines and prostate cancer cell lines at five dose concentrations with GI(50) values of 0.34 and 0.31 mu M, respectively. (C) 2013 Elsevier Ltd. All rights reserved.
• INHIBITORS OF 11-BETA-HYDROXY STEROID DEHYDROGENASE TYPE 1 AND TYPE 2
  申请人：Sterix Limited

  公开号：EP1556040A1

  公开（公告）日：2005-07-27
• US7309715B2
  申请人：——

  公开号：US7309715B2

  公开（公告）日：2007-12-18