1,3-dihydro-2-<2-(dimethylamino)ethyl>-2H-benzimidazol-2-one | 131637-64-4

• 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: 1,3-dihydro-2-<2-(dimethylamino)ethyl>-2H-benzimidazol-2-one
• 英文别名: 1-(2-(dimethylamino)ethyl)-1,3-dihydro-2H-benzo[d]imidazole-2-one；1,3-dihydro-1-(2-dimethylaminoethyl)-2H-benzimidazol-2-one；1-[2-(dimethylamino)ethyl]-1,3-dihydrobenzimidazol-2-one；3-[2-(dimethylamino)ethyl]-1H-benzimidazol-2-one
• CAS: 131637-64-4
• 化学式: C₁₁H₁₅N₃O
• 分子量: 205.26
• InChiKey: JSTZYOFLAQAJDC-UHFFFAOYSA-N

物化性质

• 熔点：
  108-110 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dihydro-2-<2-(dimethylamino)ethyl>-2H-benzimidazol-2-one 在 copper(l) iodide 、 potassium tert-butylate 、 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.67h， 生成 1-{3-[4-(2-Chloro-phenyl)-9-methyl-6H-1-thia-5,7,8,9a-tetraaza-cyclopenta[e]azulen-2-yl]-prop-2-ynyl}-3-(2-dimethylamino-ethyl)-1,3-dihydro-benzoimidazol-2-one
  参考文献：
  名称：

  Triazolobenzo- and triazolothienodiazepines as potent antagonists of platelet activating factor

  摘要：

  A series of [1,2,4]triazolo[4,3-alpha][1,4]benzodiazepines bearing an ethynyl functionality at the 8-position and the isosteric thieno[3,2-f][1,2,4]triazolo[4,3-alpha][1,4]diazepines were prepared and evaluated as antagonists of platelet activating factor. The effects of substitution were explored in in vitro and in vivo test systems designed to measured PAF-antagonistic activity. Results are discussed and compared with previously published data. Many of the compounds had activity superior to WEB 2086, compound 1. In general, the thieno analogues exhibited better oral activity than the corresponding benzodiazepines. The duration of activity upon oral administration was modulated by the substitution on the acetylenic side chain. Compounds 71 and 81 were selected for further pharmacological evaluation as a result of their good oral potency and exceptionally long duration of action.

  DOI：

  10.1021/jm00107a048
• 作为产物：
  描述：

  N-(2-aminophenyl)-2-(dimethylamino)ethylamine hydrochloride 在 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.5h， 以50%的产率得到1,3-dihydro-2-<2-(dimethylamino)ethyl>-2H-benzimidazol-2-one
  参考文献：
  名称：

  Triazolobenzo- and triazolothienodiazepines as potent antagonists of platelet activating factor

  摘要：

  A series of [1,2,4]triazolo[4,3-alpha][1,4]benzodiazepines bearing an ethynyl functionality at the 8-position and the isosteric thieno[3,2-f][1,2,4]triazolo[4,3-alpha][1,4]diazepines were prepared and evaluated as antagonists of platelet activating factor. The effects of substitution were explored in in vitro and in vivo test systems designed to measured PAF-antagonistic activity. Results are discussed and compared with previously published data. Many of the compounds had activity superior to WEB 2086, compound 1. In general, the thieno analogues exhibited better oral activity than the corresponding benzodiazepines. The duration of activity upon oral administration was modulated by the substitution on the acetylenic side chain. Compounds 71 and 81 were selected for further pharmacological evaluation as a result of their good oral potency and exceptionally long duration of action.

  DOI：

  10.1021/jm00107a048

文献信息

• [EN] 1,3,4-OXADIAZOLE DERIVATIVE COMPOUNDS AS HISTONE DEACETYLASE 6 INHIBITOR, AND THE PHARMACEUTICAL COMPOSITION COMPRISING THE SAME<br/>[FR] COMPOSÉS DÉRIVÉS DE 1,3,4-OXADIAZOLE UTILISÉS COMME INHIBITEURS D'HISTONE DÉSACÉTYLASE 6, ET COMPOSITION PHARMACEUTIQUE LES COMPRENANT
  申请人：CHONG KUN DANG PHARMACEUTICAL CORP

  公开号：WO2020240492A1

  公开（公告）日：2020-12-03

  The present invention relates to 1,3,4-oxadiazole derivative compounds having a histone deacetylase 6 (HDAC6) inhibitory activity, stereoisomers thereof or pharmaceutically acceptable salts thereof, a use thereof in preparation of a medicament, a pharmaceutical composition comprising the same, a therapeutic method using the composition, and a method for preparing the same, and the 1,3,4-oxadiazole derivative compounds are represented by a following chemical formula (I).

  本发明涉及具有组蛋白去乙酰化酶6（HDAC6）抑制活性的1,3,4-噁二唑衍生物化合物，其立体异构体或其药学上可接受的盐，以及其在药物制备中的用途，包括相同的药物组成、使用该组成的治疗方法，以及制备该组成的方法，其中1,3,4-噁二唑衍生物化合物由以下化学式（I）表示。
• Benzimidazolinone derivatives
  申请人：Yamanouchi Pharmaceutical Co., Ltd.

  公开号：US05162318A1

  公开（公告）日：1992-11-10

  Benzimidazolinone derivatives of the general formula (I): ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each is a hydrogen or halogen atom or a lower alkyl, halo-lower alkyl, hydroxy-lower alkyl, hydroxyl, lower alkoxy, aryloxy, acyl, cyano, carboxyl, a lower alkoxycarbonyl, carbamoyl, nitro or nitrogen-containing 5- or 6-membered heterocyclic group; A is an ethylene group which may optionally have at least one branch; R.sup.4 and R.sup.5, which may be the same or different, each is a lower alkyl group or R.sup.4 and R.sup.5, together with the adjacent nitrogen atom, represent a pyrrolidinyl, piperidino or a morpholino group provided that when ##STR2## is a piperidino or diethylamino group, at least one of R.sup.1, R.sup.2 and R.sup.3 is other than a hydrogen atom, or pharmaceutically acceptable salts thereof, methods of producing the same and pharmaceutical compositions containing the same are disclosed. Pharmacologically, the above compounds (I) have pulmonary surfactant secretion promoting activity.

  通式（I）的苯并咪唑啉衍生物：##STR1## 其中R.sup.1，R.sup.2和R.sup.3，可以相同或不同，分别是氢原子或卤素原子或较低的烷基，卤代较低的烷基，羟基较低的烷基，羟基，较低的烷氧基，芳氧基，酰基，氰基，羧基，较低的烷氧羰基，氨基甲酰基，硝基或含氮的5或6元杂环基；A是乙烯基，可以选择性地具有至少一个支链；R.sup.4和R.sup.5，可以相同或不同，分别是较低的烷基或R.sup.4和R.sup.5与相邻的氮原子一起表示吡咯啉基，哌啶基或吗啉基，但当##STR2##为哌啶基或二乙基氨基基团时，R.sup.1，R.sup.2和R.sup.3中至少有一个不是氢原子，或其药学上可接受的盐，公开了制备上述化合物（I）的方法和包含它们的制药组合物。从药理学角度来看，上述化合物（I）具有促进肺表面活性物质分泌的活性。
• Sulfonyldihydrobenzimidazolone compounds as 5-hydroxytryptamine-6 ligands
  申请人：Cole Cecil Derek

  公开号：US20050020575A1

  公开（公告）日：2005-01-27

  The present invention provides a compound of formula I and the use thereof in the therapeutic treatment of a central nervous system disorder related to or affected by the 5-HT6 receptor.

  本发明提供了一种I式化合物及其在治疗与5-HT6受体相关或受其影响的中枢神经系统疾病中的用途。
• HETEROCYCLIC AMIDE COMPOUNDS AS PROTEIN KINASE INHIBITORS
  申请人：Reddy Panduranga Adulla P.

  公开号：US20100286135A1

  公开（公告）日：2010-11-11

  The present invention relates to novel heterocyclic amide compounds of Formula I: as disclosed herein or a pharmaceutically acceptable salt, solvate, ester, prodrug or stereoisomer thereof. Also disclosed are compositions comprising said compounds, and methods for using said compounds for treating or preventing a proliferative disease, an anti-proliferative disorder, inflammation, arthritis, a neurological or neurodegenerative disease, a cardiovascular disease, alopecia, a neuronal disease, an ischemic injury, a viral disease or a fungal disease.

  本发明涉及公式I的新异环酰胺化合物，如本文所述或其药学上可接受的盐、溶剂化物、酯、前药或立体异构体。还公开了包含该化合物的组合物，并且公开了使用该化合物治疗或预防增殖性疾病、抗增殖性障碍、炎症、关节炎、神经或神经退行性疾病、心血管疾病、脱发、神经元疾病、缺血性损伤、病毒性疾病或真菌病的方法。
• [EN] HETEROCYCLIC AMIDE COMPOUNDS AS PROTEIN KINASE INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES D'AMIDE EN TANT QU'INHIBITEURS DE PROTÉINE KINASE
  申请人：SCHERING CORP

  公开号：WO2009014637A3

  公开（公告）日：2009-03-19