(9ci)-5-氯-1-甲基-1H-苯并咪唑-2-胺 | 103748-25-0

• 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: (9ci)-5-氯-1-甲基-1H-苯并咪唑-2-胺
• 英文名称: 5-chloro-1-methyl-1H-benzimidazol-2-amine
• 英文别名: 2-amino-1-methyl-5-chlorobenzimidazole；2-amino-5-chloro-1-methylbenzimidazole；5-chloro-1-methylbenzimidazol-2-amine
• CAS: 103748-25-0
• 化学式: C₈H₈ClN₃
• mdl: MFCD01658290
• 分子量: 181.625
• InChiKey: QZDYOBDSZXQLIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 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：

  5-氯-2-甲氧基苯甲醛 、 (9ci)-5-氯-1-甲基-1H-苯并咪唑-2-胺 在 sodium tetrahydroborate 作用下， 以 甲醇 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  In vitro activity of new N-benzyl-1H-benzimidazol-2-amine derivatives against cutaneous, mucocutaneous and visceral Leishmania species

  摘要：

  The identification of specific therapeutic targets and the development of new drugs against leishmaniasis are urgently needed, since chemotherapy currently available for its treatment has several problems including many adverse side effects. In an effort to develop new antileishmanial drugs, in the present study a series of 28 N-benzyl-1H-benzimidazol-2-amine derivatives was synthesized and evaluated in vitro against Leishmania mexicana promastigotes. Compounds 7 and 8 with the highest antileishmanial activity (micromolar) and lower cytotoxicity than miltefosine and amphotericin B were selected to evaluate their activity against L braziliensis 9 and L donovani, species causative of mucocutaneous and visceral leishmaniasis, respectively. Compound 7 showed significantly higher activity against L. braziliensis promastigotes than compound 8 and slightly lower than miltefosine. Compounds 7 and 8 had 1050 values in the micromolar range against the amastigote of L mexicana and L braziliensis. However, both compounds did not show better activity against L donovani than miltefosine. Compound 8 showed the highest SI against both parasite stages of L mexicana. In addition, compound 8 inhibited 68.27% the activity of recombinant L mexicana arginase (LmARG), a therapeutic target for the treatment of leishmaniasis. Docking studies were also performed in order to establish the possible mechanism of action by which this compound exerts its inhibitory effect. Compound 8 shows promising potential for the development of more potent antileishmanial benzimidazole derivatives. (C) 2017 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.exppara.2017.11.009
• 作为产物：
  描述：

  2,5-二氯硝基苯 在 盐酸 、 氢气 、 铜 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 异丙醇 为溶剂， 20.0~100.0 ℃ 、101.33 kPa 条件下， 反应 27.5h， 生成 (9ci)-5-氯-1-甲基-1H-苯并咪唑-2-胺
  参考文献：
  名称：

  Discovery of 2-iminobenzimidazoles as potent hepatitis C virus inhibitors with a novel mechanism of action

  摘要：

  In this report we describe 2-iminobenzimidazole (IBI) analogs, identified during the course of a phenotypic high-throughput screening campaign, as novel hepatitis C virus (HCV) inhibitors. A series of IBI derivatives was synthesized and evaluated for their inhibitory activity against infectious HCV. Among the IBIs derivatives studied in this work, we identified promising compounds with high antiviral efficacy, high selectivity index and good microsomal stability. Noteworthy, the IBI series exhibited inhibitory activity on early and late steps of the viral cycle, but not in the HCV replicon system demonstrating a mechanism of action distinct from clinical-stage and approved anti-HCV drugs. Overall, our results suggest that IBIs are predestinated for further exploration as lead compounds for novel HCV interventions. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.030

文献信息

• [EN] HETEROCYCLIC COMPOUNDS CONTAINING AN INDOLE CORE<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES CONTENANT UN COEUR INDOLE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2011071716A1

  公开（公告）日：2011-06-16

  Disclosed are novel compounds which inhibit RSK, methods of making such compounds and pharmaceutical compositions comprising such compounds. Also disclosed are methods of treating RSK2 regulated disorders using compounds of the invention.

  公开了抑制RSK的新颖化合物，制造此类化合物的方法以及包含此类化合物的药物组合物。还公开了使用本发明的化合物治疗RSK2调控失调的方法。
• A Facile Synthesis of 2-Aminobenzoxazoles and 2-Aminobenzimidazoles Using N-Cyano-N-phenyl-p-toluenesulfonamide (NCTS) as an Efficient Electrophilic Cyanating Agent
  作者：Mahesh Kasthuri、H. Babu、K. Kumar、Ch. Sudhakar、P. Kumar

  DOI：10.1055/s-0034-1380166

  日期：——

  A facile synthesis of 2-aminobenzoxazole and 2-aminobenz­imidazole derivatives employing a nonhazardous electrophilic cyanating agent: N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) with various substituted 2-aminophenols and benzene-1,2-diamine derivatives in the presence of lithium hexamethyldisilazide (LiHMDS) is described. This novel protocol boasts operational simplicity, shorter reaction time,

  使用无害的亲电氰化剂轻松合成 2-氨基苯并恶唑和 2-氨基苯并咪唑衍生物：N-氰基-N-苯基-对甲苯磺酰胺（NCTS）与各种取代的 2-氨基苯酚和苯-1,2-二胺衍生物描述了六甲基二硅叠氮化锂 (LiHMDS) 的存在。这种新颖的协议具有操作简单、反应时间更短和检查简单的特点。
• COMPOUNDS AND METHODS FOR KINASE MODULATION, AND INDICATIONS THEREFOR
  申请人：Ibrahim Prabha N.

  公开号：US20110183988A1

  公开（公告）日：2011-07-28

  Compounds and salts thereof, formulations thereof, conjugates thereof, derivatives thereof, forms thereof and uses thereof are described. In certain aspects and embodiments, the described compounds or salts thereof, formulations thereof, conjugates thereof, derivatives thereof, forms thereof are active on each of B-Raf, B-Raf V600E and c-Raf-1 protein kinase. In certain aspects and embodiments, the described compounds are active in inhibiting proliferation of a Ras mutant cell line. Also described are methods of use thereof to treat diseases and conditions, including melanoma, glioma, glioblastoma, pilocytic astrocytoma, liver cancer, biliary tract cancer, cholangiocarcinoma, colorectal cancer, lung cancer, bladder cancer, gallbladder cancer, breast cancer, pancreatic cancer, thyroid cancer, kidney cancer, ovarian cancer, adrenocortical cancer, prostate cancer, gastrointestinal stromal tumors, medullary thyroid cancer, tumor angiogenesis, acute myeloid leukemia, chronic myelomonocytic leukemia, childhood acute lymphoblastic leukemia, plasma cell leukemia, and multiple myeloma.

  描述了化合物及其盐、制剂、共轭物、衍生物、形式和用途。在某些方面和实施例中，所述的化合物或其盐、制剂、共轭物、衍生物、形式对B-Raf、B-Raf V600E和c-Raf-1蛋白激酶均具有活性。在某些方面和实施例中，所述的化合物在抑制Ras突变细胞系增殖方面具有活性。还描述了使用它们治疗疾病和病况的方法，包括黑色素瘤、胶质瘤、胶质母细胞瘤、毛细胞星形细胞瘤、肝癌、胆管癌、胆管细胞癌、结直肠癌、肺癌、膀胱癌、胆囊癌、乳腺癌、胰腺癌、甲状腺癌、肾癌、卵巢癌、肾上腺皮质癌、前列腺癌、胃肠道间质瘤、髓样甲状腺癌、肿瘤血管生成、急性髓系白血病、慢性髓细胞/单核细胞白血病、儿童急性淋巴细胞白血病、浆细胞白血病和多发性骨髓瘤。
• HETEROCYCLIC COMPOUNDS CONTAINING AN INDOLE CORE
  申请人：Boyer Stephen James

  公开号：US20130109679A1

  公开（公告）日：2013-05-02

  Disclosed are novel compounds which inhibit RSK, methods of making such compounds and pharmaceutical compositions comprising such compounds. Also disclosed are methods of treating RSK2 regulated disorders using compounds of the invention.

  本发明揭示了一种新型化合物，可抑制RSK，制备这种化合物的方法以及包含这种化合物的药物组合物。本发明还揭示了使用本发明化合物治疗RSK2调节的疾病的方法。
• Benzoxadiazocines, benzothiadiazocines and benzotriazocines-V
  作者：Ferenc Bertha、Gyula Hornyák、Károly Zauer、Antal Feller、Károly Lempert、Etelka Pjecka、Gabor Tóth

  DOI：10.1016/s0040-4020(01)96604-9

  日期：1985.1