1-(5-azido-6-chloropyridin-3-ylmethyl)-5-methyl-2-nitroiminohexahydro-1,3,5-triazine | 321845-18-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(5-azido-6-chloropyridin-3-ylmethyl)-5-methyl-2-nitroiminohexahydro-1,3,5-triazine
• 英文别名: (NE)-N-[1-[(5-azido-6-chloropyridin-3-yl)methyl]-5-methyl-1,3,5-triazinan-2-ylidene]nitramide
• CAS: 321845-18-5
• 化学式: C₁₀H₁₂ClN₉O₂
• 分子量: 325.717
• InChiKey: VVSILLNKACHHGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(5-azido-6-chloropyridin-3-ylmethyl)-5-methyl-2-nitroiminohexahydro-1,3,5-triazine 、 碘甲烷 在 18-冠醚-6 、 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以84%的产率得到1-(5-azido-6-chloropyridin-3-ylmethyl)-3,5-dimethyl-2-nitroiminohexahydro-1,3,5-triazine
  参考文献：
  名称：

  5-Azidoimidacloprid and an Acyclic Analogue as Candidate Photoaffinity Probes for Mammalian and Insect Nicotinic Acetylcholine Receptors

  摘要：

  The 5-azido analogue:of:the major, insecticide imidacloprid, 1-(5-azido-6-chloropyridin-3-ylmethy)-2-nitroiminoimidazolidine (1), and an acyclic analogue, N-(5-azido-6-chloropyridin-3-ylmethyl)-N'-methyl-N " -nitroguanidine (2), were prepared in good yields as candidate photoaffinity probes for mammalian and insect nicotinic acetylcholine receptors (nAChRs). The essential intermediate was 5-azido-6-chloropyridin-3-ylmethyl chloride (3) prepared in two: ways: from, 6-chloro-5-nitronicotinic acid by selective reduction and then diazotization, and from N-(6-chloropyridin-3-ylmethyl)morpholine by an electrophilic azide introduction with lithium diisopropylamide: followed by,chlorine substitution of morpholine with Ethyl chloroformate: Coupling of 3 with 2-nitroiminoimidazolidine gave 1, Conversion of 3 to 2 was achieved in good,yields via the hexahydrotriazine intermediate 14. Fortuitously, the azido substituent in land 2 increases' the affinity 7-79-fold for rat brain and recombinant (alpha4 beta2 nAChRs:(K(i)s 4.4-60 nM competing with [H-3](-)-nicotine) while maintaining high potency on both insect nAChRs (Drosophila and Myzus) (K(i)s 1-5 nM competing with [H-3]imidacloprid). Azidopyridinyl compounds 1 and 2 are therefore candidate photoaffinity probes for characterization. of both mammalian and insect receptors.

  DOI：

  10.1021/jm000240p
• 作为产物：
  描述：

  2-氯-5-氯甲基吡啶 在 正丁基锂 、 氯甲酸乙酯 、 sodium hydride 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 35.33h， 生成 1-(5-azido-6-chloropyridin-3-ylmethyl)-5-methyl-2-nitroiminohexahydro-1,3,5-triazine
  参考文献：
  名称：

  5-Azidoimidacloprid and an Acyclic Analogue as Candidate Photoaffinity Probes for Mammalian and Insect Nicotinic Acetylcholine Receptors

  摘要：

  The 5-azido analogue:of:the major, insecticide imidacloprid, 1-(5-azido-6-chloropyridin-3-ylmethy)-2-nitroiminoimidazolidine (1), and an acyclic analogue, N-(5-azido-6-chloropyridin-3-ylmethyl)-N'-methyl-N " -nitroguanidine (2), were prepared in good yields as candidate photoaffinity probes for mammalian and insect nicotinic acetylcholine receptors (nAChRs). The essential intermediate was 5-azido-6-chloropyridin-3-ylmethyl chloride (3) prepared in two: ways: from, 6-chloro-5-nitronicotinic acid by selective reduction and then diazotization, and from N-(6-chloropyridin-3-ylmethyl)morpholine by an electrophilic azide introduction with lithium diisopropylamide: followed by,chlorine substitution of morpholine with Ethyl chloroformate: Coupling of 3 with 2-nitroiminoimidazolidine gave 1, Conversion of 3 to 2 was achieved in good,yields via the hexahydrotriazine intermediate 14. Fortuitously, the azido substituent in land 2 increases' the affinity 7-79-fold for rat brain and recombinant (alpha4 beta2 nAChRs:(K(i)s 4.4-60 nM competing with [H-3](-)-nicotine) while maintaining high potency on both insect nAChRs (Drosophila and Myzus) (K(i)s 1-5 nM competing with [H-3]imidacloprid). Azidopyridinyl compounds 1 and 2 are therefore candidate photoaffinity probes for characterization. of both mammalian and insect receptors.

  DOI：

  10.1021/jm000240p

文献信息

• 5-Azidoimidacloprid and an Acyclic Analogue as Candidate Photoaffinity Probes for Mammalian and Insect Nicotinic Acetylcholine Receptors
  作者：Shinzo Kagabu、Peter Maienfisch、Aiguo Zhang、Joaquin Granda-Minones、Joerg Haettenschwiler、Hartmut Kayser、Thomas Maetzke、John E. Casida

  DOI：10.1021/jm000240p

  日期：2000.12.1

  The 5-azido analogue:of:the major, insecticide imidacloprid, 1-(5-azido-6-chloropyridin-3-ylmethy)-2-nitroiminoimidazolidine (1), and an acyclic analogue, N-(5-azido-6-chloropyridin-3-ylmethyl)-N'-methyl-N " -nitroguanidine (2), were prepared in good yields as candidate photoaffinity probes for mammalian and insect nicotinic acetylcholine receptors (nAChRs). The essential intermediate was 5-azido-6-chloropyridin-3-ylmethyl chloride (3) prepared in two: ways: from, 6-chloro-5-nitronicotinic acid by selective reduction and then diazotization, and from N-(6-chloropyridin-3-ylmethyl)morpholine by an electrophilic azide introduction with lithium diisopropylamide: followed by,chlorine substitution of morpholine with Ethyl chloroformate: Coupling of 3 with 2-nitroiminoimidazolidine gave 1, Conversion of 3 to 2 was achieved in good,yields via the hexahydrotriazine intermediate 14. Fortuitously, the azido substituent in land 2 increases' the affinity 7-79-fold for rat brain and recombinant (alpha4 beta2 nAChRs:(K(i)s 4.4-60 nM competing with [H-3](-)-nicotine) while maintaining high potency on both insect nAChRs (Drosophila and Myzus) (K(i)s 1-5 nM competing with [H-3]imidacloprid). Azidopyridinyl compounds 1 and 2 are therefore candidate photoaffinity probes for characterization. of both mammalian and insect receptors.