3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-pyridine | 155473-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-pyridine
• 英文别名: 3-(4,5-Dihydro-1H-imidazol-2-ylmethyl)-pyridin；2-(3-pyridyl)methyl-2-imidazoline；3-(4,5-dihydro-1H-imidazol-2-ylmethyl)pyridine
• CAS: 155473-69-1
• 化学式: C₉H₁₁N₃
• 分子量: 161.206
• InChiKey: QARDLIPNCAPWCY-UHFFFAOYSA-N

物化性质

• 熔点：
  68-70 °C
• 沸点：
  165-170 °C(Press: 1 Torr)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氯-3-硝基吡啶 、 3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-pyridine 以 乙腈 为溶剂， 以32%的产率得到4-Pyridin-3-yl-1,2-dihydro-3,5,9,9b-tetraaza-cyclopenta[a]naphthalene 5-oxide
  参考文献：
  名称：

  Parthasarathy, P. C.; Iyer, Suresh; Hendi, Mukta, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 12, p. 1233 - 1235

  摘要：

  DOI：
• 作为产物：
  描述：

  3-吡啶乙腈 、 N-甲苯磺酰基乙二胺 生成 3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-pyridine
  参考文献：
  名称：

  Protiva et al., Chemicke Listy, 1952, vol. 46, p. 640,643

  摘要：

  DOI：

文献信息

• Cyclic amidine compounds
  申请人：——

  公开号：US20030100769A1

  公开（公告）日：2003-05-29

  There is provided cyclic amidine compounds of the following formula (I): 1 wherein: A 1 and A 2 are hydrogen atom, optionally substituted alkyl group; optionally substituted aryl group; or optionally substituted heterocyclic group; and X is —C(R 1 ,R 2 )—C(R 3 ,R 4 )—, —C(R 5 )═C(R 6 )—, —C(R 7 ,R 8 )—C(R 9 ,R 10 )—C(R 11 ,R 12 )—, or —C(R 13 ,R 14 )—C(R 15 ,R 16 )—NH— (wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are hydrogen atom; halogen atom; optionally substituted alkyl group; optionally substituted aryl group; or optionally substituted heterocyclic group; or pharmaceutically acceptable salts thereof. These compounds have good affinity for &agr;4&bgr;2 nicotinic acetylcholine receptors and activate the same to thereby exert a preventive or therapeutic effect on cerebral dysfunction.

  提供了以下式子（I）的环状腙类化合物：1其中：A1和A2为氢原子，可选取代烷基，可选取代芳基或可选取代杂环基；X为—C（R1，R2）—C（R3，R4）—，—C（R5）═C（R6）—，—C（R7，R8）—C（R9，R10）—C（R11，R12）—或—C（R13，R14）—C（R15，R16）—NH—（其中，R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15和R16为氢原子，卤素原子，可选取代烷基，可选取代芳基或可选取代杂环基）或其药学上可接受的盐。这些化合物对α4β2型尼古丁乙酰胆碱受体具有良好的亲和力，并激活该受体，从而对脑功能障碍产生预防或治疗作用。
• Homoazanicotine:  A Structure-Affinity Study for Nicotinic Acetylcholine (nACh) Receptor Binding
  作者：G. Ferretti、M. Dukat、M. Giannella、A. Piergentili、M. Pigini、W. Quaglia、M. I. Damaj、B. R. Martin、R. A. Glennon

  DOI：10.1021/jm020188s

  日期：2002.10.1

  We have recently identified 3-[(1-methyl)-4,5-dihydro-1H-imidazol-2-yl)methyl]pyridine (homo-azanicotine, 8) as a novel nicotinic acetylcholinergic (nACh) receptor ligand. In the present investigation, after we determined that 8 binds selectively at nicotinic (K-i = 7.8 nM) vs muscarinic (K-i > 10 000 nM) acetylcholinergic receptors, we examined its structure-affinity relationships for nACh receptor binding. The features investigated included the influence of (i) the composition of connector that separates the two rings, (ii) the N-methyl group, (iii) the ring opening of the imidazoline ring, (iv) the pyridine nitrogen atom, and (v) the aromatization of the imidazoline ring on nACh receptor affinity. As with nicotine, the parent structure seems optimal and most structural changes reduce nACh receptor affinity. Also, as with nicotine analogues, alteration of the spacer group influences affinity in a manner that is somewhat different than that seen with the parent structure.
• Binding of nicotine and homoazanicotine analogues at neuronal nicotinic acetylcholinergic (nACh) receptors
  作者：G. Ferretti、M. Dukat、M. Giannella、A. Piergentili、M. Pigini、W. Quaglia、M.I. Damaj、B.R. Martin、R.A. Glennon

  DOI：10.1016/s0960-894x(02)01031-4

  日期：2003.2

  A total of 20 substituted analogues of nicotine (1a) and homoazanicotine (3a) were examined in order to determine whether or not they might bind in a similar manner at alpha4beta2 nicotinic acetocholinergic (nACh) receptors. It was found that parallel structural changes in the two series resulted in parallel shifts in affinity. Evidence suggests that the two series are binding in a comparable fashion. (C) 2003 Elsevier Science Ltd. All rights reserved.
• CYCLIC AMIDINE COMPOUNDS AND THEIR USE AS ALPHA4BETA2 NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS
  申请人：SUNTORY LIMITED

  公开号：EP1280793A2

  公开（公告）日：2003-02-05
• [EN] NOVEL BIOREDUCTIVE AGENTS<br/>[FR] NOUVEAUX AGENTS BIOREDUCTEURS
  申请人：BRITISH TECHNOLOGY GROUP LIMITED

  公开号：WO1994006797A1

  公开（公告）日：1994-03-31

  (EN) Quinoxaline or pyrido pyrazine derivatives of formula (I) wherein R1 is: hydrogen, alkyl, alkoxy, alkylamino, dialkylamino, aminoalkylamino, aminoalkyl(N-alkyl)amino or aminoalkoxy unsubstituted or substituted on the terminal amino group by one or two alkyl groups or a divalent group which forms a saturated heterocyclic ring together with the nitrogen atom to which it is attached, hydroxyalkylamino or haloalkylamino or an N-alkyl derivative thereof, or hydroxyalkoxy or haloalkoxy; a heterocyclic group which is a 1-pyrrolidino, 1-piperidino, 1-morpholino group, unsubstituted or substituted; or a 1-piperazino group which is unsubstituted or substituted substituents in the 2- or 3-position and in the 4-position is unsubstituted or N-substituted by haloalkyl, cycloalkyl, pyridyl or phenyl; R2 is a hydrocarbyl or heterocyclyl aromatic group unsubstituted or substituted; X is -CH= or -N=; and X1 is hydrogen or halogen; and pharmaceutically acceptable salts thereof are useful in the treatment of tumours, and in particular hypoxic tumours. Processes for producing the compounds and pharmaceutical compositions comprising them.(FR) L'invention concerne des dérivés de la quinoxaline ou de la pyridopyrazine de la formule (I). Dans cette formule R1 représente: un hydrogène, un alkyle, un alcoxy, un alkylamino, un dialkylamino, un aminoalkylamino, un aminoalkyl(N-alkyl)amino ou un aminoalcoxy non substitué ou substitué sur le groupe amino terminal par un ou deux groupes alkyle ou un groupe divalent qui forme un cycle hétérocyclique saturé avec l'atome d'azote auquel il est fixé, un hydroxyalkylamino ou un haloalkylamino ou son dérivé N-alkyle, ou un hydroxyalcoxy ou un haloalcoxy; un groupe hétérocyclique qui est un groupe 1-pyrrolidino, 1-pipéridino, 1-morpholino, non substitué ou substitué; ou un groupe 1-pipérazino qui est non substitué ou substitué en position 2 ou 3, non substitué en position 4 ou N-substitué par un groupe haloalkyle, cycloalkyle, pyridyle ou phényle; R2 représente un groupe aromatique hydrocarbyle ou hétérocyclyle non substitué ou substitué; X représente -CH= ou -N=; et X1 représente un hydrogène ou un halogène. L'invention concerne l'utilisation de ces dérivés et de leurs sels acceptables sur le plan pharmaceutique dans le traitement de tumeurs et en particulier de tumeurs hypoxiques. L'invention concerne également des procédés pour produire ces composés et des compositions pharmaceutiques les contenant.