[4-(3,4-Diaminophenyl)piperazin-1-yl]-(1-hydroxynaphthalen-2-yl)methanone | 98526-54-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [4-(3,4-Diaminophenyl)piperazin-1-yl]-(1-hydroxynaphthalen-2-yl)methanone
• CAS: 98526-54-6
• 化学式: C₂₁H₂₂N₄O₂
• 分子量: 362.431
• InChiKey: YPGAYQCCLNEENT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  95.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-二羧甲基-2-甲基-2-硫代异脲 、 [4-(3,4-Diaminophenyl)piperazin-1-yl]-(1-hydroxynaphthalen-2-yl)methanone 以 乙醇 为溶剂， 反应 8.0h， 以35%的产率得到methyl N-[6-[4-(1-hydroxynaphthalene-2-carbonyl)piperazin-1-yl]-1H-benzimidazol-2-yl]carbamate
  参考文献：
  名称：

  Synthesis and anthelmintic activity of 5(6)-[(benzimidazol-2-yl)carboxamido]- and (4-substituted piperazin-1-yl)benzimidazoles

  摘要：

  The synthesis of alkyl 5(6)-(benzimidazol-2-ylcarbamoyl)benzimidazole-2-carbamates (6, 7), and alkyl 5(6)-(4-substituted piperazin-1-yl)benzimidazole-2-carbamates (31-40) has been carried out. When the compounds were tested for their anthelmintic activity against Ancylostoma ceylanicum in hamsters, Hymenolepis nana in rats, Litomosoides carinii in cotton rats, and Dipetalonema viteae in Mastomys natalensis, methyl 5(6)-(4-benzoylpiperazin-1-yl)benzimidazole-2-carbamate (31), methyl 5(6)-[4-(2-furoyl)piperazin-1-yl]benzimidazole-2-carbamate and methyl 5(6)-[4-[(diethylamino)carbonyl]piperazin-1-yl]benzimidazole- -2-carbamate (36) showed 100% elimination of tapeworms H. nana at three oral doses of 100-250 mg/kg. Compounds 34 and 36 also killed the microfilariae and adult worms of L. carinii in cotton rats at an intraperitoneal dose of 30 mg/kg given for 5 days.

  DOI：

  10.1021/jm00149a036
• 作为产物：
  描述：

  [4-(3-Amino-4-nitro-phenyl)-piperazin-1-yl]-(1-hydroxy-naphthalen-2-yl)-methanone 在 镍 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以45%的产率得到[4-(3,4-Diaminophenyl)piperazin-1-yl]-(1-hydroxynaphthalen-2-yl)methanone
  参考文献：
  名称：

  Synthesis and anthelmintic activity of 5(6)-[(benzimidazol-2-yl)carboxamido]- and (4-substituted piperazin-1-yl)benzimidazoles

  摘要：

  The synthesis of alkyl 5(6)-(benzimidazol-2-ylcarbamoyl)benzimidazole-2-carbamates (6, 7), and alkyl 5(6)-(4-substituted piperazin-1-yl)benzimidazole-2-carbamates (31-40) has been carried out. When the compounds were tested for their anthelmintic activity against Ancylostoma ceylanicum in hamsters, Hymenolepis nana in rats, Litomosoides carinii in cotton rats, and Dipetalonema viteae in Mastomys natalensis, methyl 5(6)-(4-benzoylpiperazin-1-yl)benzimidazole-2-carbamate (31), methyl 5(6)-[4-(2-furoyl)piperazin-1-yl]benzimidazole-2-carbamate and methyl 5(6)-[4-[(diethylamino)carbonyl]piperazin-1-yl]benzimidazole- -2-carbamate (36) showed 100% elimination of tapeworms H. nana at three oral doses of 100-250 mg/kg. Compounds 34 and 36 also killed the microfilariae and adult worms of L. carinii in cotton rats at an intraperitoneal dose of 30 mg/kg given for 5 days.

  DOI：

  10.1021/jm00149a036

文献信息

• [DE] NEUE ANTHRACEN-DERIVATE UND DEREN VERWENDUNG ALS ARZNEIMITTEL<br/>[EN] NOVEL ANTHRACENE DERIVATIVES AND THE USE THEREOF AS A MEDICAMENT<br/>[FR] NOUVEAUX DERIVES D'ANTHRACENE ET LEUR UTILISATION COMME MEDICAMENTS
  申请人：ZENTARIS GMBH

  公开号：WO2004007470A1

  公开（公告）日：2004-01-22

  Die Erfindung betrifft neue Anthracen-Derivate der Allgemeinen Formel (I), deren Herstellung und Verwendung als Arzneimittel, insbesondere zur Behandlung von Tumoren.

  这项发明涉及一种新的通用式(I)的蒽衍生物，其制备和用作药物，特别是用于治疗肿瘤。
• New anthracene derivatives and their use as pharmaceutical preparations
  申请人：——

  公开号：US20040110756A1

  公开（公告）日：2004-06-10

  The invention relates to new anthracene derivatives of the general Formula 1 and to their synthesis and use as pharmaceutical preparations, especially for the treatment of a tumor. 1

  本发明涉及通式 1 的新蒽衍生物及其合成和用作药物制剂，特别是用于治疗肿瘤。 1
• DUBEY, RASHMI;ABUZAR, SYED;SHARMA, SATYAVAN;CHATTERJEE, R. K.;KATIYAR, J.+, J. MED. CHEM., 1985, 28, N 11, 1748-1750
  作者：DUBEY, RASHMI、ABUZAR, SYED、SHARMA, SATYAVAN、CHATTERJEE, R. K.、KATIYAR, J.+

  DOI：——

  日期：——
• NEUE ANTHRACEN-DERIVATE UND DEREN VERWENDUNG ALS ARZNEIMITTEL
  申请人：Zentaris GmbH

  公开号：EP1521748A1

  公开（公告）日：2005-04-13
• Synthesis and anthelmintic activity of 5(6)-[(benzimidazol-2-yl)carboxamido]- and (4-substituted piperazin-1-yl)benzimidazoles
  作者：Rashmi Dubey、Syed Abuzar、Satyavan Sharma、R. K. Chatterjee、J. C. Katiyar

  DOI：10.1021/jm00149a036

  日期：1985.11

  The synthesis of alkyl 5(6)-(benzimidazol-2-ylcarbamoyl)benzimidazole-2-carbamates (6, 7), and alkyl 5(6)-(4-substituted piperazin-1-yl)benzimidazole-2-carbamates (31-40) has been carried out. When the compounds were tested for their anthelmintic activity against Ancylostoma ceylanicum in hamsters, Hymenolepis nana in rats, Litomosoides carinii in cotton rats, and Dipetalonema viteae in Mastomys natalensis, methyl 5(6)-(4-benzoylpiperazin-1-yl)benzimidazole-2-carbamate (31), methyl 5(6)-[4-(2-furoyl)piperazin-1-yl]benzimidazole-2-carbamate and methyl 5(6)-[4-[(diethylamino)carbonyl]piperazin-1-yl]benzimidazole- -2-carbamate (36) showed 100% elimination of tapeworms H. nana at three oral doses of 100-250 mg/kg. Compounds 34 and 36 also killed the microfilariae and adult worms of L. carinii in cotton rats at an intraperitoneal dose of 30 mg/kg given for 5 days.