3-{[4'-amino-5'-(3'',4'',5''-trimethoxybenzyl)pyrimidin-2'-yl]imino}-5-chloro-1,3-dihydro-2H-indol-2-one | 269738-95-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-{[4'-amino-5'-(3'',4'',5''-trimethoxybenzyl)pyrimidin-2'-yl]imino}-5-chloro-1,3-dihydro-2H-indol-2-one
• 英文别名: (3Z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-chloro-1H-indol-2-one
• CAS: 269738-95-6
• 化学式: C₂₂H₂₀ClN₅O₄
• 分子量: 453.885
• InChiKey: WNRZWHGBQGJXES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-{[4'-amino-5'-(3'',4'',5''-trimethoxybenzyl)pyrimidin-2'-yl]imino}-5-chloro-1,3-dihydro-2H-indol-2-one 、 聚合甲醛 、 2-甲基哌啶 以 乙醇 、 水 为溶剂， 以71.5%的产率得到(3Z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-chloro-1-[(2-methyl-1-piperidyl)methyl]indolin-2-one
  参考文献：
  名称：

  Isatin Mannich碱的合成，抗病毒和抗菌活性

  摘要：

  HIV是许多机会性感染（例如肺结核，肝炎，细菌感染等）的最重要风险因素。我们设计了一种伊斯兰定铅化合物作为一种新型的非核苷逆转录酶抑制剂，具有广谱化学治疗特性，可有效治疗AIDS和AIDS-相关的机会感染。化合物1-环丙基-6-氟-1,4-二氢-4-氧代-7-[[N4- [3'-（4'-氨基-5'-三甲氧基苄基嘧啶-2'-基）亚氨基-1' -（5-氯异丁烯基）[甲基] -N1-哌嗪基] -3-喹啉羧酸（14）成为对HIV，HCV， 结核分枝杆菌 和各种病原菌具有活性的最有效的广谱化学治疗剂 。

  DOI：

  10.1007/s00044-005-0135-x
• 作为产物：
  描述：

  5-氯靛红 、 甲氧苄啶 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以84.2%的产率得到3-{[4'-amino-5'-(3'',4'',5''-trimethoxybenzyl)pyrimidin-2'-yl]imino}-5-chloro-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  Isatin Mannich碱的合成，抗病毒和抗菌活性

  摘要：

  HIV是许多机会性感染（例如肺结核，肝炎，细菌感染等）的最重要风险因素。我们设计了一种伊斯兰定铅化合物作为一种新型的非核苷逆转录酶抑制剂，具有广谱化学治疗特性，可有效治疗AIDS和AIDS-相关的机会感染。化合物1-环丙基-6-氟-1,4-二氢-4-氧代-7-[[N4- [3'-（4'-氨基-5'-三甲氧基苄基嘧啶-2'-基）亚氨基-1' -（5-氯异丁烯基）[甲基] -N1-哌嗪基] -3-喹啉羧酸（14）成为对HIV，HCV， 结核分枝杆菌 和各种病原菌具有活性的最有效的广谱化学治疗剂 。

  DOI：

  10.1007/s00044-005-0135-x

文献信息

• Synthesis, antibacterial, antifungal and anti-HIV activities of norfloxacin Mannich bases
  作者：Surendra N Pandeya、Dhamrajan Sriram、Gopal Nath、Erik De Clercq

  DOI：10.1016/s0223-5234(00)00125-2

  日期：2000.2

  Mannich bases of norfloxacin were synthesized by reacting them with formaldehyde and several isatin derivatives. Their chemical structures have been confirmed by means of their IR, H-1-NMR data and by elemental analysis. Investigation of in vitro antimicrobial activity of compounds was done by the agar dilution method against 28 pathogenic bacteria, eight pathogenic fungi and anti-HIV activity against replication of HIV-1 (III B) in MT-4 cells. The in vivo antibacterial efficacy of selected derivatives was determined using a mouse infection model. All the synthesized compounds are more active than norfloxacin against the 13 bacteria tested. The compounds are also more active than the standard drug clotrimazole against Histoplasma capsulatum. Two compounds S-8 and S-9 have shown inhibition against HIV-1 (III B) with EC50 values of 11.3 and 13.9 mu g/mL, respectively. In the mouse protection test, two compounds S-4 (ED50: 1.25 mg/kg) and S-9 (ED50: 1.62 mg/kg) are more active than norfloxacin (ED50: 6mg/kg). Among the compounds tested, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7[[N-4-[5'-bromo-3'-(4'-amino-5'-trimethoxybenzylpyrimidin-2'-yl]-imino-1'-isatinyl]methyl]N-1-piperazinyl]-3-quinoline carboxylicacid (S-9) showed promising activity in all the three tests. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
• Synthesis, Antiviral and Antibacterial Activities of Isatin Mannich Bases
  作者：Dharmarajan Sriram、Tanushree Ratan Bal、Perumal Yogeeswari

  DOI：10.1007/s00044-005-0135-x

  日期：2005.6

  HIV is the most significant risk factor for many opportunistic infections like tuberculosis, hepatitis, bacterial infections etc. We designed an isatin lead compound as a novel non-nucleoside reverse transcriptase inhibitor with broad-spectrum chemotherapeutic properties for the effective treatment of AIDS and AIDS-related opportunistic infections. Compound 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo

  HIV是许多机会性感染（例如肺结核，肝炎，细菌感染等）的最重要风险因素。我们设计了一种伊斯兰定铅化合物作为一种新型的非核苷逆转录酶抑制剂，具有广谱化学治疗特性，可有效治疗AIDS和AIDS-相关的机会感染。化合物1-环丙基-6-氟-1,4-二氢-4-氧代-7-[[N4- [3'-（4'-氨基-5'-三甲氧基苄基嘧啶-2'-基）亚氨基-1' -（5-氯异丁烯基）[甲基] -N1-哌嗪基] -3-喹啉羧酸（14）成为对HIV，HCV， 结核分枝杆菌 和各种病原菌具有活性的最有效的广谱化学治疗剂 。