1-苄基-2-甲基-1H-1,3-苯并咪唑-5-胺 | 14624-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1-苄基-2-甲基-1H-1,3-苯并咪唑-5-胺
• 英文名称: 1-benzyl-2-methyl-1H-benzimidazol-5-ylamine
• 英文别名: 5-Amino-1-benzyl-2-methyl-1H-benzimidazole；1-benzyl-2-methyl-1H-benzoimidazol-5-ylamine；5-amino-1-benzyl-2-methylbenzimidazole；1-Benzyl-2-methyl-5-aminobenzimidazol；1-benzyl-2-methyl-1H-1,3-benzimidazol-5-amine；1-benzyl-2-methylbenzimidazol-5-amine
• CAS: 14624-97-6
• 化学式: C₁₅H₁₅N₃
• mdl: MFCD04539177
• 分子量: 237.304
• InChiKey: CNNHMFSRMLZBIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  1-苄基-2-甲基-1H-1,3-苯并咪唑-5-胺 在 碳酸氢钠 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 (3-benzyl-2-methyl-3H-benzimidazol-5-yl)-[4-(4-methyl-piperazin-1-yl)-6-morpholin-4-yl-[1,3,5]triazin-2-yl]-amine
  参考文献：
  名称：

  Triazine–benzimidazole hybrids: Anticancer activity, DNA interaction and dihydrofolate reductase inhibitors

  摘要：

  A new series of triazine-benzimidazole hybrids has been synthesized with different substitution of primary and secondary amines at one of the position of triazine in moderate to good yields. These compounds were evaluated for their inhibitory activities over 60 human tumor cell lines at one dose and five dose concentrations. Compounds 6b, 8 and 9 showed broad spectrum of antitumor activities with GI(50) values of 9.79, 2.58 and 3.81 mu M, respectively. DNA binding studies also indicated strong interaction properties of these compounds. These synthesized compounds also showed inhibition of mammalian dihydrofolate reductase (DHFR). Compound 6b was depicted as the most active member of DHFR inhibitor with IC50 value of 1.05 mu M. Molecular modelling studies were used to identify the stabilized interactions of Compound 6b within the active site of enzyme for DHFR. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.03.012
• 作为产物：
  描述：

  2-甲基-5-硝基苯并咪唑 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 1-苄基-2-甲基-1H-1,3-苯并咪唑-5-胺
  参考文献：
  名称：

  Garuti; Giovanninetti; Ferranti, Pharmazie, 1987, vol. 42, # 6, p. 378 - 381

  摘要：

  DOI：

文献信息

• Synthesis, in vitro antitumor activity, dihydrofolate reductase inhibition, DNA intercalation and structure–activity relationship studies of 1,3,5-triazine analogues
  作者：Prinka Singla、Vijay Luxami、Kamaldeep Paul

  DOI：10.1016/j.bmcl.2015.11.083

  日期：2016.1

  values of 1.77, 1.94 and 2.87 μM, respectively. The synthesized compounds were then evaluated for their inhibitory activity to mammalian dihydrofolate reductase. Compound 22 was depicted as the most active compound for the inhibition of dihydrofolate reductase with IC50 value of 2.0 nM. DNA binding studies were also revealed strong interacting properties of triazine derivatives towards calf thymus-DNA

  已经设计和合成了一系列被4-氟苯胺取代的三嗪-苯并咪唑。这些化合物进一步被不同的伯胺和仲胺取代。新合成的化合物的结构通过1 H，13 C NMR，质谱确定，对于化合物18，通过单晶X射线衍射分析确定。以一剂和五剂浓度水平针对60种人类肿瘤细胞系评估了新合成的化合物。化合物7，8和22已被发现是最活跃的抗肿瘤剂与GI 50值分别为1.77、1.94和2.87μM。然后评估合成的化合物对哺乳动物二氢叶酸还原酶的抑制活性。化合物22被描述为抑制二氢叶酸还原酶的最具活性的化合物，IC 50值为2.0 nM。DNA结合研究还揭示了三嗪衍生物与小牛胸腺DNA的强相互作用特性。
• [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。
• Imidazoindoles
  作者：V. P. Chetverikov、Yu. I. Ostapovich、A. N. Kost、N. Ya. Maksimov、T. N. Ozeredenko

  DOI：10.1007/bf00475395

  日期：1980.1
• CHETVERIKOV V. P.; OSTAPOVICH YU. I.; KOST A. N.; MAKSIMOV N. YA.; OZERED+, XIMIYA GETEROTSIKL. SOEDIN., 1980, HO 1, 74-78
  作者：CHETVERIKOV V. P.、 OSTAPOVICH YU. I.、 KOST A. N.、 MAKSIMOV N. YA.、 OZERED+

  DOI：——

  日期：——