1-allyl-2-methyl-5-nitro-1H-benzo[d]imidazole | 1434623-20-7

• 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: 1-allyl-2-methyl-5-nitro-1H-benzo[d]imidazole
• 英文别名: 1-allyl-2-methyl-5-nitro-1H-benzimidazole；2-Methyl-5-nitro-1-prop-2-enylbenzimidazole
• CAS: 1434623-20-7
• 化学式: C₁₁H₁₁N₃O₂
• 分子量: 217.227
• InChiKey: YSVFQQWVKMZGAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 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：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-allyl-2-methyl-5-nitro-1H-benzo[d]imidazole 在 盐酸 、 tin(II) chloride dihdyrate 作用下， 以 水 、 异丙醇 为溶剂， 反应 7.0h， 生成 (1-allyl-2-methyl-1H-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
• 作为产物：
  描述：

  2-甲基苯并咪唑 在 硫酸 、 硝酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 1-allyl-2-methyl-5-nitro-1H-benzo[d]imidazole
  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。
• Synthesis,<i>in vitro</i>and<i>in vivo</i>antitumor and antiviral activity of novel 1-substituted benzimidazole derivatives
  作者：Yasser M. Shaker、Mohamed A. Omar、Khaled Mahmoud、Salwa M. Elhallouty、Waled M. El-Senousy、Mamdouh M. Ali、Abeer E. Mahmoud、Abeer H. Abdel-Halim、Saeed M. Soliman、Hoda I. El Diwani

  DOI：10.3109/14756366.2014.979344

  日期：2015.9.3

  5-nitro-1H-benzimidazole derivatives substituted at position 1 by heterocyclic rings was synthesized. Cytotoxicity and antiviral activity of the new compounds were tested. Compound 3 was more active than doxorubicin against A-549, HCT-116 and MCF-7. However, compound 3 showed no activity against human liver carcinoma Hep G-2 cell line. Compounds 9 and 17b (E) showed potency near to doxorubicin against the four

  合成了一系列新的5-硝基-1H-苯并咪唑衍生物，这些衍生物在1位被杂环取代。测试了新化合物的细胞毒性和抗病毒活性。化合物3比阿霉素对A-549，HCT-116和MCF-7的活性更高。然而，化合物3对人肝癌Hep G-2细胞系没有活性。化合物9和17b（E）对四细胞系显示出接近阿霉素的效价。体内测定化合物9对大鼠肝癌的急性毒性。有趣的是，与DENA诱导的荷癌大鼠相比，它显示出肝功能和病理学恢复正常的活性。化合物17a（Z），17b（E）和18a（Z）因其针对轮状病毒Wa株的抗病毒活性而成为最有前途的化合物。
• 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。
• 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