1-[(imidazolidin-2-yl)imino]benzimidazole | 1034876-65-7

• 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-[(imidazolidin-2-yl)imino]benzimidazole
• 英文别名: 1-[(Imidazolidin-2-yl)imino]benzimidazole hydrochloride；N-(4,5-dihydro-1H-imidazol-2-yl)benzimidazol-1-amine
• CAS: 1034876-65-7
• 化学式: C₁₀H₁₁N₅
• 分子量: 201.231
• InChiKey: BBZKMBYUAONEMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(imidazolidin-2-yl)imino]benzimidazole 在 盐酸 作用下， 以 甲醇 为溶剂， 以59%的产率得到1-[(imidazolidin-2-yl)imino]benzimidazole hydrochloride
  参考文献：
  名称：

  1-[(Imidazolidin-2-yl)imino]indazole. Highly α₂/I₁ Selective Agonist: Synthesis, X-ray Structure, and Biological Activity

  摘要：

  Novel benzazole derivatives bearing a (imidazolidin-2-yl)imino moiety at position I or 2 were synthesized by reacting 1-amino- or 2-aminobenzazoles with N,N'-bis(tert-butoxycarbonyl)imidazolidine-2-thione in the presence of HgCl2. Structures of 1-[(imidazolidin-2-yl)imino]indazole (marsanidine, 13a) and free base of the 4-Cl derivative 12e were confirmed by X-ray single crystal structure analysis. Compound 13a was found to be the selective alpha(2)-adrenoceptor ligand with alpha(2)-adrenoceptor/imidazoline I-1 receptor selectivity ratio of 3879, while 1-[(imidazolidin-2-yl)imino]-7-methylindazole (13k) proved to be a mixed alpha(2)-adrenoceptor/imidazoline I-1 receptor agonist with alpha 2/I-1 selectivity ratio of 7.2. Compound 13k when administered intravenously to male Wistar rats induced a dose-dependent decrease in mean arterial blood pressure (ED50 = 0.6 mu g/kg) and heart rate, which was attenuated following pretreatment with alpha(2A)-adrenoceptor antagonist RX821002. Compound 13a may find a variety of medical uses ascribed to alpha(2)-adrenoceptor agonists, and its 7-methyl derivative 13k is a good candidate for development as a centrally acting antihypertensive drug.

  DOI：

  10.1021/jm800112s
• 作为产物：
  描述：

  1-{[1,3-di(tert-butoxycarbonyl)imidazolidin-2-yl]imino}benzimidazole 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到1-[(imidazolidin-2-yl)imino]benzimidazole
  参考文献：
  名称：

  1-[(Imidazolidin-2-yl)imino]indazole. Highly α₂/I₁ Selective Agonist: Synthesis, X-ray Structure, and Biological Activity

  摘要：

  Novel benzazole derivatives bearing a (imidazolidin-2-yl)imino moiety at position I or 2 were synthesized by reacting 1-amino- or 2-aminobenzazoles with N,N'-bis(tert-butoxycarbonyl)imidazolidine-2-thione in the presence of HgCl2. Structures of 1-[(imidazolidin-2-yl)imino]indazole (marsanidine, 13a) and free base of the 4-Cl derivative 12e were confirmed by X-ray single crystal structure analysis. Compound 13a was found to be the selective alpha(2)-adrenoceptor ligand with alpha(2)-adrenoceptor/imidazoline I-1 receptor selectivity ratio of 3879, while 1-[(imidazolidin-2-yl)imino]-7-methylindazole (13k) proved to be a mixed alpha(2)-adrenoceptor/imidazoline I-1 receptor agonist with alpha 2/I-1 selectivity ratio of 7.2. Compound 13k when administered intravenously to male Wistar rats induced a dose-dependent decrease in mean arterial blood pressure (ED50 = 0.6 mu g/kg) and heart rate, which was attenuated following pretreatment with alpha(2A)-adrenoceptor antagonist RX821002. Compound 13a may find a variety of medical uses ascribed to alpha(2)-adrenoceptor agonists, and its 7-methyl derivative 13k is a good candidate for development as a centrally acting antihypertensive drug.

  DOI：

  10.1021/jm800112s

文献信息

• Novel benzimidazole derivatives
  申请人：Synaptic Pharmaceutical Corporation

  公开号：US20030022927A1

  公开（公告）日：2003-01-30

  This invention provides compounds having the structure: 1 wherein each of R 1 , R 2 , R 3 and R 9 is independently H; straight chain or branched, substituted or unsubstituted , C 1 -C 7 , alkyl, C 2 -C 7 alkenyl or alkynyl; C 3 -C 7 cycloalkyl or cycloalkenyl; acyl, phenyl, substituted phenyl, or heteroaryl; wherein each dashed line represents a single bond or a double bond with the proviso that if R 1 is present, R 3 is absent and there is a double bond between N at position 3 and C at position 2 and a single bond between C at position 2 and N at position 1 and if R 3 is present, R 1 is absent and there is a double bond between N at position 1 and C at position 2 and a single bond between C at position 2 and N at position 3; wherein each of R 4 , R 5 and R 6 is independently H, F, Cl, Br, I; straight chain or branched, substituted or unsubstituted C 1 -C 7 , alkyl, C 2 -C, alkenyl or alkynyl; C 3 -C 7 cycloalkyl or cycloalkenyl; phenyl, substituted phenyl, heteroaryl, —OH, —OR 7 , —CN, —COR 7 , —COR 2 , —CON(R 7 ) 2 , —OCOR 7 , —SR 7 , —N(R 7 ) 2 , —NR 7 COR 7 , —(CH 2 ) n OR 7 , —(CH 2 ) n N (R 7 ) 2 , —(CH 2 ) n NR 7 COR 7 , wherein n is an integer from 1 to 4; and wherein each of R 7 and R 8 is independently H; straight chain or branched, substituted or unsubstituted C 1 -C 7 alkyl, C 2 -C 7 alkenyl or alkynyl; phenyl or substituted phenyl. These compounds are selective for cloned human alpha 2 receptors and are useful as analgesic, sedative or anaesthetic agents.

  本发明提供了具有以下结构的化合物：1其中R1、R2、R3和R9中的每一个都是独立的H；直链或支链，取代或未取代的C1-C7烷基，C2-C7烯基或炔基；C3-C7环烷基或环烯基；酰基，苯基，取代苯基或杂环基；其中每个虚线代表单键或双键，但如果R1存在，则R3不存在，在位置3的N和位置2的C之间有双键，在位置2的C和位置1的N之间有单键，如果R3存在，则R1不存在，在位置1的N和位置2的C之间有双键，在位置2的C和位置3的N之间有单键；其中R4、R5和R6中的每一个都是独立的H、F、Cl、Br、I；直链或支链，取代或未取代的C1-C7烷基，C2-C7烯基或炔基；C3-C7环烷基或环烯基；苯基，取代苯基，杂环基，-OH，-OR7，-CN，-COR7，-COR2，-CON（R7）2，-OCOR7，-SR7，-N（R7）2，-NR7COR7，-（CH2）nOR7，-（CH2）nN（R7）2，-（CH2）nNR7COR7，其中n是1至4的整数；其中R7和R8中的每一个都是独立的H；直链或支链，取代或未取代的C1-C7烷基，C2-C7烯基或炔基；苯基或取代苯基。这些化合物对克隆的人类α2受体具有选择性，并可用作镇痛剂、镇静剂或麻醉剂。
• NOVEL BENZIMIDAZOLE DERIVATIVES
  申请人：SYNAPTIC PHARMACEUTICAL CORPORATION

  公开号：EP0775134A1

  公开（公告）日：1997-05-28
• US3935314A
  申请人：——

  公开号：US3935314A

  公开（公告）日：1976-01-27
• 1-[(Imidazolidin-2-yl)imino]indazole. Highly α₂/I₁ Selective Agonist: Synthesis, X-ray Structure, and Biological Activity
  作者：Franciszek Sa̧czewski、Anita Kornicka、Apolonia Rybczyńska、Alan L. Hudson、Shu Sean Miao、Maria Gdaniec、Konrad Boblewski、Artur Lehmann

  DOI：10.1021/jm800112s

  日期：2008.6.1

  Novel benzazole derivatives bearing a (imidazolidin-2-yl)imino moiety at position I or 2 were synthesized by reacting 1-amino- or 2-aminobenzazoles with N,N'-bis(tert-butoxycarbonyl)imidazolidine-2-thione in the presence of HgCl2. Structures of 1-[(imidazolidin-2-yl)imino]indazole (marsanidine, 13a) and free base of the 4-Cl derivative 12e were confirmed by X-ray single crystal structure analysis. Compound 13a was found to be the selective alpha(2)-adrenoceptor ligand with alpha(2)-adrenoceptor/imidazoline I-1 receptor selectivity ratio of 3879, while 1-[(imidazolidin-2-yl)imino]-7-methylindazole (13k) proved to be a mixed alpha(2)-adrenoceptor/imidazoline I-1 receptor agonist with alpha 2/I-1 selectivity ratio of 7.2. Compound 13k when administered intravenously to male Wistar rats induced a dose-dependent decrease in mean arterial blood pressure (ED50 = 0.6 mu g/kg) and heart rate, which was attenuated following pretreatment with alpha(2A)-adrenoceptor antagonist RX821002. Compound 13a may find a variety of medical uses ascribed to alpha(2)-adrenoceptor agonists, and its 7-methyl derivative 13k is a good candidate for development as a centrally acting antihypertensive drug.