(3-allyl-2-methyl-3H-benzimidazol-5-yl)-(2-chloroquinazolin-4-yl)amine | 1434623-48-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (3-allyl-2-methyl-3H-benzimidazol-5-yl)-(2-chloroquinazolin-4-yl)amine
• 英文别名: 2-chloro-N-(2-methyl-3-prop-2-enylbenzimidazol-5-yl)quinazolin-4-amine
• CAS: 1434623-48-9
• 化学式: C₁₉H₁₆ClN₅
• 分子量: 349.823
• InChiKey: UHJKZAQSOIFFFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 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：
  55.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-allyl-2-methyl-3H-benzimidazol-5-yl)-(2-chloroquinazolin-4-yl)amine 、 2,6-二氟苯胺 以 异丙醇 为溶剂， 以70%的产率得到N⁴-(3-allyl-2-methyl-3H-benzimidazol-5-yl)-N²-(2,6-difluorophenyl)quinazolin-2,4-diamine
  参考文献：
  名称：

  Synthesis and in vitro antitumor evaluation of primary amine substituted quinazoline linked benzimidazole

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2013.12.005
• 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 、 异丙醇 为溶剂， 反应 15.0h， 生成 (3-allyl-2-methyl-3H-benzimidazol-5-yl)-(2-chloroquinazolin-4-yl)amine
  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

• Quinazoline–benzimidazole hybrid as dual optical sensor for cyanide and Pb2+ ions and Aurora kinase inhibitor
  作者：Vijay Luxami、Richa Rani、Alka Sharma、Kamaldeep Paul

  DOI：10.1016/j.jphotochem.2015.05.025

  日期：2015.10

  Compounds 1 and 2 exhibited selective fluorescence response toward Pb2+ over the other metal ions like Zn2+, Co2+, Ca2+, K+, Ni2+, Mn2+, Fe2+, Hg2+, Na+ etc. Compound 1 behaved as cyanide selective chromofluorescent sensor amongst other anions like F-, Cl-, Br-, I-, AcO-, H2PO4-, HSO4- etc. The binding properties of compounds 1 and 2 with cyanide and Pb2+ were investigated via UV-vis, fluorescence spectroscopy, H-1 NMR titration experiment and DFT calculations. Compound 1 has been used to estimate CN- ion (2-500 mu M) and compound 2 used to estimate Pb2+ ion (0.05-1500 mu M) ratiometrically. Compounds 1 and 2 have also been used as Aurora kinase inhibitors with IC50 values of 7.50 mu M and 0.53 mu M, respectively. (C) 2015 Elsevier B.V. All rights reserved.
• Synthesis, single crystal and antitumor activities of benzimidazole–quinazoline hybrids
  作者：Alka Sharma、Vijay Luxami、Kamaldeep Paul

  DOI：10.1016/j.bmcl.2013.03.107

  日期：2013.6

  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.
• 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.