1-吡嗪-2-基-1,4-二氮杂烷 | 502133-53-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1-吡嗪-2-基-1,4-二氮杂烷
• 英文名称: 1-(pyrazin-2-yl)-1,4-diazepane
• 英文别名: 1-Pyrazin-2-yl-1,4-diazepane
• CAS: 502133-53-1
• 化学式: C₉H₁₄N₄
• mdl: MFCD05182299
• 分子量: 178.237
• InChiKey: ZIPUZQXWPDCSAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  41
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-吡嗪-2-基-1,4-二氮杂烷 、 Boc-(R)-3-氨基-4-(2,4,5-三氟苯基)丁酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 tert-butyl (R)-(4-oxo-4-(4-(pyrazin-2-yl)-1,4-diazepan-1-yl)-1-(2,4,5-trifluorophenyl)butan-2-yl)carbamate
  参考文献：
  名称：

  Synthesis and biological evaluation of homopiperazine derivatives with β-aminoacyl group as dipeptidyl peptidase IV inhibitors

  摘要：

  Compounds with homopiperazine skeleton are designed to find a potent DPP-IV inhibitor without inhibiting CYP. Thus a series of beta-aminoacyl-containing homopiperazine derivatives was synthesized and evaluated. Compounds with acid moiety were found to be potent inhibitors of DPP-IV without inhibiting CYP 3A4. More specifically, compound 7m showed nanomolar activity with no inhibition towards five subtypes of CYPs, was considered as a prototype for further derivatization. Based on its X-ray co-crystal structure with human DPP-IV, we identified compounds 7s and 7t which showed good in vitro activity, no CYP inhibition, and good selectivity.

  DOI：

  10.1016/j.bmcl.2008.10.076
• 作为产物：
  描述：

  tert-Butyl 4-Pyrazin-2-yl-1,4-diazepane-1-carboxylate 在 盐酸 、 水 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 生成 1-吡嗪-2-基-1,4-二氮杂烷
  参考文献：
  名称：

  Synthesis and biological evaluation of homopiperazine derivatives with β-aminoacyl group as dipeptidyl peptidase IV inhibitors

  摘要：

  Compounds with homopiperazine skeleton are designed to find a potent DPP-IV inhibitor without inhibiting CYP. Thus a series of beta-aminoacyl-containing homopiperazine derivatives was synthesized and evaluated. Compounds with acid moiety were found to be potent inhibitors of DPP-IV without inhibiting CYP 3A4. More specifically, compound 7m showed nanomolar activity with no inhibition towards five subtypes of CYPs, was considered as a prototype for further derivatization. Based on its X-ray co-crystal structure with human DPP-IV, we identified compounds 7s and 7t which showed good in vitro activity, no CYP inhibition, and good selectivity.

  DOI：

  10.1016/j.bmcl.2008.10.076

文献信息

• [EN] ANTIBIOTIC RESISTANCE BREAKERS<br/>[FR] AGENTS DE RUPTURE DE RÉSISTANCE AUX ANTIBIOTIQUES
  申请人：KING S COLLEGE LONDON

  公开号：WO2018220365A1

  公开（公告）日：2018-12-06

  The invention relates to antibiotic compounds of formula (A1) and pharmaceutically acceptable salts, solvates, tautomers and combinations thereof, wherein X and L are optional linkers and one of RA or R1 comprises Ar1, wherein Ar1 is an antibiotic resistance breaker moiety which comprises an optionally substituted C6-10 aryl, C7-13 aralkyl, C5-10 heteroaryl, C6-13 heteroaralkyl, C5-10 heterocyclyl, C6-13 heterocyclalkyl, C3-10 carbocyclyl, C4-13 carbocyclalkyl, -C(=NR')-NR'R'' or –CH2- CH=CH2 group; wherein after administration of the compound to a bacterial infection this moiety reduces or prevents efflux. The invention also discloses pharmaceutical compositions comprising compounds of formula (A1) and the use of such compounds as medicaments, in particular, to treat bacterial infections, such as drug-resistant bacterial infections.

  该发明涉及公式（A1）的抗生素化合物及其药学上可接受的盐、溶剂化合物、互变异构体和它们的组合，其中X和L是可选的连接物，RA或R1中的一个包括Ar1，其中Ar1是一种抗生素耐药性破坏基团，包括可选择取代的C6-10芳基，C7-13芳基烷基，C5-10杂芳基，C6-13杂芳基烷基，C5-10杂环烷基，C6-13杂环烷基，C3-10碳环烷基，C4-13碳环烷基，-C(=NR')-NR'R''或–CH2- CH=CH2基团；在将该化合物用于细菌感染后，该基团减少或预防外流。该发明还公开了包括公式（A1）化合物的药物组合物以及将这些化合物用作药物的用途，特别是用于治疗细菌感染，如耐药性细菌感染。
• Synthesis and biological evaluation of homopiperazine derivatives with β-aminoacyl group as dipeptidyl peptidase IV inhibitors
  作者：Jin Hee Ahn、Woul Seong Park、Mi Ae Jun、Mi Sik Shin、Seung Kyu Kang、Ki Young Kim、Sang Dal Rhee、Myung Ae Bae、Kwang Rok Kim、Sung Gyu Kim、Sun Young Kim、Sang Kwon Sohn、Nam Sook Kang、Jie Oh Lee、Duck Hyung Lee、Hyae Gyeong Cheon、Sung Soo Kim

  DOI：10.1016/j.bmcl.2008.10.076

  日期：2008.12

  Compounds with homopiperazine skeleton are designed to find a potent DPP-IV inhibitor without inhibiting CYP. Thus a series of beta-aminoacyl-containing homopiperazine derivatives was synthesized and evaluated. Compounds with acid moiety were found to be potent inhibitors of DPP-IV without inhibiting CYP 3A4. More specifically, compound 7m showed nanomolar activity with no inhibition towards five subtypes of CYPs, was considered as a prototype for further derivatization. Based on its X-ray co-crystal structure with human DPP-IV, we identified compounds 7s and 7t which showed good in vitro activity, no CYP inhibition, and good selectivity.