2-(2-chlorophenyl)-N-cyclohexyl-5-methylimidazo[1,2-a]pyridin-3-amine | 1152030-26-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-chlorophenyl)-N-cyclohexyl-5-methylimidazo[1,2-a]pyridin-3-amine
• CAS: 1152030-26-6
• 化学式: C₂₀H₂₂ClN₃
• 分子量: 339.868
• InChiKey: FKSAWGDCELGVTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-chlorophenyl)-N-cyclohexyl-5-methylimidazo[1,2-a]pyridin-3-amine 在 4-methylbenzenesulfonic acid hydrate 、 碘苯二乙酸 作用下， 反应 1.5h， 以81.6%的产率得到2-(2-chlorophenyl)-N-cyclohexyl-2-oxoacetamide
  参考文献：
  名称：

  一种α-羰基酰胺衍生物的制备方法

  摘要：

  本发明公开了一种α‑羰基酰胺衍生物的制备方法，即：采用吡啶并咪唑胺类化合物与水在氧化剂作用下发生开环反应，同时插入氧原子，制备得到α‑羰基酰胺衍生物的方法。本方法操作简单，底物普适性广，反应过程中无金属催化，不需要无水无氧的条件，其结构中“O”原子来源于水，副产物可作为制备本发明所采用吡啶并咪唑胺类的原料，从而实现其再循环利用。本方法还具有收率高、可用于大量制备α‑羰基酰胺衍生物和制备部分现有方法中较难制备α‑羰基酰胺衍生物等优点。

  公开号：

  CN109096139B
• 作为产物：
  描述：

  2-氨基-6-甲基吡啶 、 异氰环已烷 、 2-氯苯甲醛 在 montmorillonite K-10 clay 作用下， 以 1,4-二氧六环 为溶剂， 以58%的产率得到2-(2-chlorophenyl)-N-cyclohexyl-5-methylimidazo[1,2-a]pyridin-3-amine
  参考文献：
  名称：

  Imidazo[1,2-a]pyridin-3-amines as potential HIV-1 non-nucleoside reverse transcriptase inhibitors

  摘要：

  During random screening of a small in-house library of compounds, certain substituted imidazo[1,2-a]pyridines were found to be weak allosteric inhibitors of HIV-1 reverse transcriptase (RT). A library of these compounds was prepared using the Groebke reaction and a subset of compounds prepared from 2-chlorobenzaldehyde, cyclohexyl isocyanide and a 6-substituted 2-aminopyridine showed good inhibitory activity in enzymatic (RT) and HIV anti-infectivity MAGI whole cell assays. The compound showing the best anti-HIV-1 IIIB whole cell activity (MAGI IC(50) = 0.18 mu M, IC(90) = 1.06 mu M), along with a good selectivity index (>800), was 2-(2-chlorophenyl)-3-(cyclohexylamino) imidazo[1,2-a]pyridine-5-carbonitrile 38. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.062

文献信息

• [EN] NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS<br/>[FR] INHIBITEURS NON NUCLÉOSIDIQUES DE LA TRANSCRIPTASE INVERSE
  申请人：SALK INSTITUITE FOR BIOLOG STU

  公开号：WO2009061856A1

  公开（公告）日：2009-05-14

  Disclosed herein are antiviral agents, in particular non-nucleoside reverse transcriptase inhibitors (NNRTIs) of the formula. Also disclosed are methods of making the NNRTIs, as well as compositions that include such NNRTIs and methods of their use for treating viral infections, in particular retroviral infections, such as HIV infection.

  本文披露了抗病毒药物，特别是式中的非核苷类逆转录酶抑制剂（NNRTIs）。还披露了制备NNRTIs的方法，以及包含这些NNRTIs的组合物和它们用于治疗病毒感染的方法，特别是逆转录病毒感染，如HIV感染。
• [EN] IMIDAZOPYRIDINES AND IMIDAZOPYRIMIDINES AS HIV-I REVERSE TRANSCRIPTASE INHIBITORS<br/>[FR] IMIDAZOPYRIDINES ET IMIDAZOPYRIMIDINES UTILISÉS COMME INHIBITEURS DE LA TRANSCRIPTASE INVERSE DU VIH-1
  申请人：CSIR

  公开号：WO2010032195A1

  公开（公告）日：2010-03-25

  The invention provides compounds of formula A or B which are useful in the treatment of a subject infected with HIV.

  这项发明提供了公式A或B的化合物，可用于治疗感染HIV的受试者。
• IMIDAZOPYRIDINES AND IMIDAZOPYRIMIDINES AS HIV-I REVERSE TRANSCRIPTASE INHIBITORS
  申请人：Bode Moira Leanne

  公开号：US20110312957A1

  公开（公告）日：2011-12-22

  The invention provides compounds of formula A or B which are useful in the treatment of a subject infected with HIV.

  本发明提供了公式A或B的化合物，其在治疗HIV感染的受试者中具有用处。
• Three Novel Sequential Reactions for the Facile Synthesis of a Library of Bisheterocycles Possessing the 3-Aminoimidazo[1,2-a]pyridine Core Cata­lyzed by Bismuth(III) Chloride
  作者：Aziz Shahrisa、Somayeh Esmati

  DOI：10.1055/s-0032-1318221

  日期：——

  Novel, one-pot, two-step, sequential protocols for the synthesis of 1,4-phenylene bisheterocyclic compounds have been developed. Successive sequencing of the Groebke-Blackburn-Bienayme reaction with Ugi-azide, Hantzsch and Biginelli reactions results in rapid and efficient formation of bisheterocyclic compounds. A simple, fast and high yielding method for the synthesis of 3-aminoimidazo[1,2-a]pyridines catalyzed by bismuth(III) chloride under solvent-free conditions is reported. Bismuth(III) chloride is also an efficient catalyst for the Ugi-azide reaction under solvent free conditions.
• NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS
  申请人：Elleder Daniel

  公开号：US20100292232A1

  公开（公告）日：2010-11-18

  Disclosed herein are antiviral agents, in particular non-nucleoside reverse transcriptase inhibitors (NNRTIs) of the formula Also disclosed are methods of making the NNRTIs, as well as compositions that include such NNRTIs and methods of their use for treating viral infections, in particular retroviral infections, such as HIV infection.