N-methylcyclohexanecarbohydrazide | 1266095-97-9

• 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: N-methylcyclohexanecarbohydrazide
• CAS: 1266095-97-9
• 化学式: C₈H₁₆N₂O
• 分子量: 156.228
• InChiKey: QNBPEDUZTLPGBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methylcyclohexanecarbohydrazide 、 氰乙酸 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.5h， 以86%的产率得到N'-(2-cyanoacetyl)-N-methylcyclohexanecarbohydrazide
  参考文献：
  名称：

  Synthesis, binding and bioactivity of γ-methylene γ-lactam ecdysone receptor ligands: Advantages of QSAR models for flexible receptors

  摘要：

  Nuclear hormone receptors, such as the ecdysone receptor, often display a large amount of induced fit to ligands. The size and shape of the binding pocket in the EcR subunit changes markedly on ligand binding, making modelling methods such as docking extremely challenging. It is, however, possible to generate excellent 3D QSAR models for a given type of ligand, suggesting that the receptor adopts a relatively restricted number of binding site configurations or 'attractors'. We describe the synthesis, in vitro binding and selected in vivo toxicity data for gamma-methylene gamma-lactams, a new class of high-affinity ligands for ecdysone receptors from Bovicola ovis (Phthiraptera) and Lucilia cuprina (Diptera). The results of a 3D QSAR study of the binding of methylene lactams to recombinant ecdysone receptor protein suggest that this class of ligands is indeed recognised by a single conformation of the EcR binding pocket. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.020
• 作为产物：
  描述：

  甲基肼 、 环己甲酰氯 以 二氯甲烷 为溶剂， 以29%的产率得到N-methylcyclohexanecarbohydrazide
  参考文献：
  名称：

  Synthesis, binding and bioactivity of γ-methylene γ-lactam ecdysone receptor ligands: Advantages of QSAR models for flexible receptors

  摘要：

  Nuclear hormone receptors, such as the ecdysone receptor, often display a large amount of induced fit to ligands. The size and shape of the binding pocket in the EcR subunit changes markedly on ligand binding, making modelling methods such as docking extremely challenging. It is, however, possible to generate excellent 3D QSAR models for a given type of ligand, suggesting that the receptor adopts a relatively restricted number of binding site configurations or 'attractors'. We describe the synthesis, in vitro binding and selected in vivo toxicity data for gamma-methylene gamma-lactams, a new class of high-affinity ligands for ecdysone receptors from Bovicola ovis (Phthiraptera) and Lucilia cuprina (Diptera). The results of a 3D QSAR study of the binding of methylene lactams to recombinant ecdysone receptor protein suggest that this class of ligands is indeed recognised by a single conformation of the EcR binding pocket. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.020

文献信息

• ARYL SUBSTITUTED 7-OXABICYCLOHEPTANE COMPOUNDS
  申请人：E.R. SQUIBB & SONS, INC.

  公开号：EP0126088A1

  公开（公告）日：1984-11-28
• US4418076A
  申请人：——

  公开号：US4418076A

  公开（公告）日：1983-11-29
• US4463015A
  申请人：——

  公开号：US4463015A

  公开（公告）日：1984-07-31
• US6326495B2
  申请人：——

  公开号：US6326495B2

  公开（公告）日：2001-12-04
• [EN] ARYL SUBSTITUTED 7-OXABICYCLOHEPTANE COMPOUNDS
  申请人：——

  公开号：WO1984000754A1

  公开（公告）日：1984-03-01

  (EN) Novel 7-oxabicycloheptane prostaglandin analogs which are cardiovascular agents useful, for example, in the treatment of thrombolytic disease. The new compounds have the structural formula (I) and including all stereoisomers thereof, wherein Z is$(6,)$-CH=N-O-(CH2)p-R4 or -(CH2)m-NH-R5; n is 1 or 2; R1 is H or lower alkyl; B is -CH=CH-, -C=C- or (CH2)2; Y is alkyl; substituted alkyl; aryl-lower alkyl; alkenyl; alkynyl; aryl; pyridyl; pyridyl-lower alkyl; substituted pyridyl; thienyl; thienylalkyl; substituted thienyl; cycloalkyl; substituted cycloalkyl; cycloalkylalkyl or substituted cycloalkylalkyl; y is 0 or 1, where y is 1, R3 is H or lower alkyl; R2 is lower alkyl, lower alkoxy, aryl, alkylamino, arylamino, aryloxy, pyridinyl or cycloalkyl or where y is 0 as indicated by$(4,)$R2 can be a -(CH)x- linking group (wherein x is 0, 3, 4 or 5) which together with-N-C-$(2,)$ may form an N-containing 5-, 6- or 7-membered heterocycle, with the proviso that when R3 is H, R2 is lower alkoxy; R4 is lower alkyl, cycloalkyl, aryl, aryl-alkyl or alkanoyl; p is 0 to 5; m is 1 to 8; and R5 is lower alkyl, lower alkoxy, aralkoxy or$(2,)$-NH-C-R6 wherein R6 is lower alkyl or phenyl. (FR) De nouveaux produits analogues de la prostaglandine 7-oxabicycloheptane sont des agents cardiovasculaires utiles par exemple pour le traitement de maladies thrombolytiques. Les nouveaux composés ont la formule (I), y compris tous ses stéréoisomères, dans laquelle Z est$(6,)$-CH=N-O-(CH2)p-R4 ou -(CH2)m-NH-R5; n est égal à 1 ou 2; R1 représente H ou un alkyl inférieur; B est -CH=CH-, -C=C- ou (CH2)2; Y est alkyl, alkyl substitué, aryl-alkyl inférieur, alkényl, alkinyl, aryl, pyridyl, pyridyl-alkyl inférieur, pyridyl substitué, thiényl, thiénylalkyl, thiényl substitué, cycloalkyl, cycloalkyl substitué, cycloalkylalkyl ou cycloalkylalkyl substitué; y est égal à 0 ou 1, et lorsque y vaut 1, R3 est H ou un alkyle inférieur; R2 est un alkyle inférieur, un alcoxy inférieur, un aryle, un alkyle amino, un aryle amino, un aryloxy, un pyridinyl ou un cycloalkyl, ou, lorsque y vaut 0 comme indiqué par$(4,)$R2 peut être un groupe de liaisons -(CH)x-, (où x vaut 0, 3, 4 ou 5) qui, avec -N-C-$(2,)$peut former un hétérocycle contenant de l'azote à 5, 6 ou 7 membres, à condition que lorsque R3 représente H, R2 est un alcoxy inférieur; R4 est un alkyle inférieur, un cycloalkyl, un aryle, un aryl-alkyl ou un alcanoyl; p est compris entre 0 et 5; m est compris entre 1 et 8; et R5 est un alkyle inférieur, un alcoxy inférieur un aralcoxy ou$(2,)$-NH-C-R6, où R6 est un phényle ou un alkyle inférieur.