2-chloromethyl-3-nitroimidazo[1,2-a]pyridine | 129179-30-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2-chloromethyl-3-nitroimidazo[1,2-a]pyridine
• 英文别名: 2-(Chloromethyl)-3-nitroimidazo[1,2-a]pyridine
• CAS: 129179-30-2
• 化学式: C₈H₆ClN₃O₂
• mdl: MFCD00269519
• 分子量: 211.608
• InChiKey: INTSNKHYSRQDPZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  63.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloromethyl-3-nitroimidazo[1,2-a]pyridine 在 sodium dithionite 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 2-{[3-(isobutylamino)imidazo[1,2-a]pyridin-2-yl]-methyl}isoindoline-1,3-dione
  参考文献：
  名称：

  Design, Synthesis, Anti-Cancer Activity, and in silico Studies of Novel Imidazo[1,2-a]pyridine Derivatives

  摘要：

  A novel series of imidazo [1,2-a]pyridine derivatives has been designed, synthesized and tested for the anti-proliferative activity against three different human cancer cell lines. Most of the synthesized compounds exhibit anti-proliferative activity with IC(50)values ranging from 5.35-59.8 mu M. Six compounds demonstrate efficient inhibition of growth of all cell lines with IC(50)values close to that of standard drug, and the compound16his more potent than the standard drug cisplatin for the HeLa cell line.

  DOI：

  10.1134/s1070363220090212
• 作为产物：
  描述：

  2-氯甲基咪唑并[1,2-a]吡啶盐酸盐 在 硫酸 、 硝酸 作用下， 反应 2.0h， 以76%的产率得到2-chloromethyl-3-nitroimidazo[1,2-a]pyridine
  参考文献：
  名称：

  合成新药RN 1咪唑并[1,2-α]吡啶的潜在药理作用

  摘要：

  2-氯甲基-3-硝基咪唑并[1,2-a]吡啶与2-硝基丙烷盐之间的S RN 1反应的研究已扩展到各种脂族，环状和杂环的硝酸根阴离子。从C-烷基化产物中，碱促进的亚硝酸消除提供了新的潜在的药理衍生物，其在2位具有三取代的双键。

  DOI：

  10.1016/s0040-4020(01)87129-5

文献信息

• Synthèse par réaction sRN1 de nouveaux dérivés en série imidazo[1,2-α]pyridine à potentialités pharmacologiques
  作者：Patrice Vanelli、Nacer Madadi、Christine Roubaud、José Maldonado、Michel P. Crozet

  DOI：10.1016/s0040-4020(01)87129-5

  日期：1991.1

  The study of SRN1 reaction between 2-chloromethyl-3-nitroimidazo[1,2-a] pyridine and 2-nitropropane salts has been extended to various aliphatic, cyclic and heterocyclic nitronate anions. From C-alkylation products, base-promoted nitrous acid elimination afforded new potential pharmacological derivatives with a trisubstituted double bond at the 2 position.

  2-氯甲基-3-硝基咪唑并[1,2-a]吡啶与2-硝基丙烷盐之间的S RN 1反应的研究已扩展到各种脂族，环状和杂环的硝酸根阴离子。从C-烷基化产物中，碱促进的亚硝酸消除提供了新的潜在的药理衍生物，其在2位具有三取代的双键。
• Electron transfer reactivity in 5-nitrouracil series
  作者：Michel P. Crozet、Armand Gellis、Christian Pasquier、Patrice Vanelle、Jean-Pierre Aune

  DOI：10.1016/0040-4039(94)02304-t

  日期：1995.1

  shown to react with various reductive alkylating agents such as p-nitrobenzyl chloride and dinitropropane by an SRN1 mechanism to give new potentially bioactive 5-nitrouracil derivatives. 1,3-Dimethyl-5-nitro-6-chloromethyluracil also reacts by an SRN1 mechanism with 2-nitropropane anion to afford a new uracil derivative bearing a trisubstituted ethylenic double bond at the 6-position.

  1，3，6-三甲基-5-硝基尿嘧啶的钠盐显示通过S RN 1机理与各种还原性烷基化剂（例如对硝基苄基氯和二硝基丙烷）反应生成新的具有潜在生物活性的5-硝基尿嘧啶衍生物。1，3-二甲基-5-硝基-6-氯甲基尿嘧啶也通过S RN 1机理与2-硝基丙烷阴离子反应，得到新的尿嘧啶衍生物，其在6-位带有三取代的烯键式双键。
• Synthesis of Diaryl-Substituted Imidazo[1,2-a]pyridines Designed as Potential Aromatase Inhibitors.
  作者：Cecile ENGUEHARD、Jean-Louis RENOU、Hassan ALLOUCHI、Jean-Michel LEGER、Alain GUEIFFIER

  DOI：10.1248/cpb.48.935

  日期：——

  From a pharmacophore model of bicyclic heterocycles as aromatase inhibitors we have designed three series of imidazo[1,2-a]pyridine derivatives. The synthesis and the spectroscopy determination of various compounds are reported. The crystal data of one of these compounds (10b) was obtained. The aromatase inhibition potency was evaluated in vitro and no activity was found.

  从双环杂环作为芳香酶抑制剂的药效团模型，我们设计了三个系列的咪唑并[1,2-a]吡啶衍生物。报道了各种化合物的合成和光谱测定。获得这些化合物（10b）之一的晶体数据。在体外评估了芳香化酶抑制能力，未发现活性。
• Targeting the human parasite Leishmania donovani: Discovery of a new promising anti-infectious pharmacophore in 3-nitroimidazo[1,2-a]pyridine series
  作者：Caroline Castera-Ducros、Lucie Paloque、Pierre Verhaeghe、Magali Casanova、Christophe Cantelli、Sébastien Hutter、Floriane Tanguy、Michèle Laget、Vincent Remusat、Anita Cohen、Maxime D. Crozet、Pascal Rathelot、Nadine Azas、Patrice Vanelle

  DOI：10.1016/j.bmc.2013.09.002

  日期：2013.11

  We report herein the discovery of antileishmanial molecules based on the imidazo[1,2-a]pyridine ring. In vitro screenings of imidazopyridines belonging to our chemical library, toward the promastigotes stage of Leishmania donovani, J774A. 1 murine and HepG2 human cells, permitted to identify three selective hit-compounds (12, 20 and 28). New derivatives were then synthesized to allow structure-activity and -toxicity relationships analyses, enabling to characterize a lead-compound (44) displaying both a high potency (IC50 = 1.8 mu M) and a good selectivity index, in comparison with three antileishmanial reference drug-compounds (amphotericin B, miltefosine and pentamidine). Moreover, lead-compound 44 also exhibits good in vitro activity against the intracellular amastigote stage of L. donovani. Thus, the 6-halo-3-nitro-2-(phenylsulfonylmethyl)imidazo[1,2-a]pyridine scaffold appears as a new promising selective antileishmanial pharmacophore, especially when substituted at position 8 by a bromine atom. (C) 2013 Elsevier Ltd. All rights reserved.
• Fast electron transfer C-alkylation of 2-nitropropane anion under microwave irradiation
  作者：Patrice Vanelle、Armand Gellis、Mustapha Kaafarani、José Maldonado、Michel P Crozet

  DOI：10.1016/s0040-4039(99)00790-x

  日期：1999.6

  Microwave irradiation is shown to be an attractive methodology for fast electron transfer C-alkylation reactions of 2-nitropropane anion by different reductive alkylating agents. This method is simple, rapid and affords excellent C-alkylation yields. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.