(2-methylimidazo[1,2-a]pyridin-3-yl)(pyridin-2-yl)methanone | 501124-58-9

• 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-methylimidazo[1,2-a]pyridin-3-yl)(pyridin-2-yl)methanone
• 英文别名: (2-Methylimidazo[1,2-a]pyridin-3-yl)(pyridin-2-yl)methanone；(2-methylimidazo[1,2-a]pyridin-3-yl)-pyridin-2-ylmethanone
• CAS: 501124-58-9
• 化学式: C₁₄H₁₁N₃O
• 分子量: 237.261
• InChiKey: HCKLVMRKHAAXHG-UHFFFAOYSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-methylimidazo[1,2-a]pyridin-3-yl)(pyridin-2-yl)methanone 在 platinum(IV) oxide 盐酸 、 氢氧化钾 、 氢气 、 一水合肼 作用下， 以 乙醇 、 二乙二醇 为溶剂， 20.0~195.0 ℃ 、303.98 kPa 条件下， 反应 4.0h， 生成 (+/-)-2-methyl-3-(piperidin-2-ylmethyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Synthesis and biological evaluation of new imidazo[1,2-a]pyridine derivatives designed as mefloquine analogues

  摘要：

  This paper describes the synthesis and the in vitro antimalarial profile of two new imidazo[1,2-a]pyridine derivatives 4.HCl and 13.HCl, structurally proposed as mefloquine (1) analogues, by exploring bioisosterism and molecular simplification tools. The synthetic route employed to access the title compounds used, as starting material, the previously described ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate derivative (5). These novel heterocyclic derivatives 4.HCl and 13.HCl presented modest antimalarial activity against the W-2 and D-6 clones of Plasmodium falciparum as well as inhibitors of in vitro heme polymerization compared to mefloquine. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0014-827x(02)01304-6
• 作为产物：
  描述：

  2-甲基吲哚[1,2-A]吡啶-3-甲醛 在 manganese(IV) oxide 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (2-methylimidazo[1,2-a]pyridin-3-yl)(pyridin-2-yl)methanone
  参考文献：
  名称：

  Synthesis and biological evaluation of new imidazo[1,2-a]pyridine derivatives designed as mefloquine analogues

  摘要：

  This paper describes the synthesis and the in vitro antimalarial profile of two new imidazo[1,2-a]pyridine derivatives 4.HCl and 13.HCl, structurally proposed as mefloquine (1) analogues, by exploring bioisosterism and molecular simplification tools. The synthetic route employed to access the title compounds used, as starting material, the previously described ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate derivative (5). These novel heterocyclic derivatives 4.HCl and 13.HCl presented modest antimalarial activity against the W-2 and D-6 clones of Plasmodium falciparum as well as inhibitors of in vitro heme polymerization compared to mefloquine. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0014-827x(02)01304-6

文献信息

• A Carbonylation Approach Toward Activation of C_sp2-H and C_sp3-H Bonds: Cu-Catalyzed Regioselective Cross Coupling of Imidazo[1,2-<i>a</i>]pyridines with Methyl Hetarenes
  作者：Sai Lei、Yingying Mai、Caijuan Yan、Jianwen Mao、Hua Cao

  DOI：10.1021/acs.orglett.6b01588

  日期：2016.8.5

  An efficient copper-catalyzed selective cross coupling of imidazo[1,2-a]pyridines with methyl hetarenes has been reported. This transformation opened a new route to synthesize the C-3 carbonyl imidazo[1,2-a]pyridine derivative, which is a common structural motif in natural products and pharmaceuticals. 18O-labeling experiments indicated that the oxygen source of products originated from O2.

  已经报道了咪唑并[1,2- a ]吡啶与甲基己烯的有效铜催化选择性交叉偶联。这种转变为合成C-3羰基咪唑并[1,2- a ]吡啶衍生物开辟了一条新途径，该衍生物是天然产物和药物中常见的结构基序。18 O-标记实验表明产物的氧源来自O 2。
• Synthesis and biological evaluation of new imidazo[1,2-a]pyridine derivatives designed as mefloquine analogues
  作者：Patricia C Lima、Mitchell A Avery、Babu L Tekwani、Helio de M Alves、Eliezer J Barreiro、Carlos A.M Fraga

  DOI：10.1016/s0014-827x(02)01304-6

  日期：2002.9

  This paper describes the synthesis and the in vitro antimalarial profile of two new imidazo[1,2-a]pyridine derivatives 4.HCl and 13.HCl, structurally proposed as mefloquine (1) analogues, by exploring bioisosterism and molecular simplification tools. The synthetic route employed to access the title compounds used, as starting material, the previously described ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate derivative (5). These novel heterocyclic derivatives 4.HCl and 13.HCl presented modest antimalarial activity against the W-2 and D-6 clones of Plasmodium falciparum as well as inhibitors of in vitro heme polymerization compared to mefloquine. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.