(E)-ethyl cinnamidate hydrochloride

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-ethyl cinnamidate hydrochloride
• 英文别名: ethyl cinnamimidate hydrochloride；(E)-ethyl cinnamimidate hydrochloride；ethyl (E)-3-phenylprop-2-enimidate;hydrochloride
• 化学式: C₁₁H₁₃NO*ClH
• 分子量: 211.691
• InChiKey: WYGDMBNWWHHXCE-NERPDURBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  33.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-ethyl cinnamidate hydrochloride 在 氨 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 12.0h， 生成 3-苯基丙烯脒
  参考文献：
  名称：

  [EN] SUBSTITUTED PYRAZOLE COMPOUNDS
  [FR] COMPOSES PYRAZOLE SUBSTITUES

  摘要：

  公开号：

  WO2007041358A3
• 作为产物：
  描述：

  肉桂腈 、 乙醇 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 (E)-ethyl cinnamidate hydrochloride
  参考文献：
  名称：

  Novel N1-(benzyl)cinnamamidine derived NR2B subtype-selective NMDA receptor antagonists

  摘要：

  Novel (E)-N-1-(benzyl)cinnamamidines were prepared and evaluated as NR2B subtype NMDA receptor ligands. Excellent affinity was achieved by appropriate substitution of either phenyl ring. The 2-methoxybenzyl compound 1h had similar to1000-fold lower IC50 in NR2B than NR2A-containing cells. Replacement of the styryl unit by 2-naphthl was well tolerated. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01060-0

文献信息

• Amidine derivatives as selective antagonists of ndma receptors
  申请人：——

  公开号：US20030119871A1

  公开（公告）日：2003-06-26

  A class of styryl amidine derivatives which are antagonists of the hum NMDA receptor, being selective for those containing the NR2B subunit, are active in the treatment and/or prevention of neurological and neurodegenerative disorders, in particular neuropathic pain and headache, specifically migraine, whils displaying fewer ataxic and related side-effects associated with other classes of NMDA receptor antagonists.

  一类苯乙烯基脲衍生物，它们是人类NMDA受体的拮抗剂，选择性作用于含有NR2B亚单位的受体，对于治疗和/或预防神经系统和神经退行性疾病，特别是神经痛和头痛，特别是偏头痛，具有较少的共济失调和其他NMDA受体拮抗剂相关的副作用。
• 7-Amino-2-phenylpyrazolo[4,3-d]pyrimidine derivatives: Structural investigations at the 5-position to target human A1 and A2A adenosine receptors. Molecular modeling and pharmacological studies
  作者：Lucia Squarcialupi、Vittoria Colotta、Daniela Catarzi、Flavia Varano、Marco Betti、Katia Varani、Fabrizio Vincenzi、Pier Andrea Borea、Nicola Porta、Antonella Ciancetta、Stefano Moro

  DOI：10.1016/j.ejmech.2014.07.060

  日期：2014.9

  In previous research, several 7-amino-2-arylpyrazolo[4,3-d]pyrimidine derivatives were identified as highly potent and selective antagonists at the human A3 adenosine receptor. Structure-activity relationship studies highlighted that affinity and selectivity depended on the nature of the substituents at the 5- and 7-positions of the pyrazolo[4,3-d]pyrimidine scaffold. In particular, small lipophilic residues at the 5-position and a free amino group at position 7 afforded compounds able to bind all four human (h) adenosine receptors. Hence, to shift affinity toward the hA1 and/or hA(2A) subtypes, alkyl and arylalkyl chains of different length were appended at position 5 of the 2-phenylpyrazolo[4,3-d]pyrimidin-7-amine. Among the new compounds, a dual hA1/hA(2A) receptor antagonist was identified, namely the 5-(3-phenylpropyl) derivative 25, which shows high affinity both at human A1 (K(i) = 5.31 nM) and A(2A) (K(i) = 55 nM) receptors. We also obtained some potent and selective antagonists for the A1 receptor, such as the 5-(3-arylpropyl)-substituted compounds 26-31, whose affinities fall in the low nanomolar range (K(i) = 0.15-18 nM). Through an in silico receptor-driven approach, the obtained binding data were rationalized and the molecular bases of the hA1 and hA(2A) AR affinity and selectivity of derivatives 25-31 are explained.
• Novel N1-(benzyl)cinnamamidine derived NR2B subtype-selective NMDA receptor antagonists
  作者：Neil R Curtis、Helen J Diggle、Janusz J Kulagowski、Clare London、Sarah Grimwood、Peter H Hutson、Fraser Murray、Pawel Richards、Alison Macaulay、Keith A Wafford

  DOI：10.1016/s0960-894x(02)01060-0

  日期：2003.2

  Novel (E)-N-1-(benzyl)cinnamamidines were prepared and evaluated as NR2B subtype NMDA receptor ligands. Excellent affinity was achieved by appropriate substitution of either phenyl ring. The 2-methoxybenzyl compound 1h had similar to1000-fold lower IC50 in NR2B than NR2A-containing cells. Replacement of the styryl unit by 2-naphthl was well tolerated. (C) 2003 Elsevier Science Ltd. All rights reserved.
• KEMPLER G.; EHRLICHMANN W.; SCHARSCHMIDT C.; DOMBROWSKI H.; GRUENERT K., WISS. Z. PAED. HOCHSCH. K. LIEBKNECHT POTSDAM, 1980, 24, NO 1, 45-56
  作者：KEMPLER G.、 EHRLICHMANN W.、 SCHARSCHMIDT C.、 DOMBROWSKI H.、 GRUENERT K.

  DOI：——

  日期：——
• NAGARAJAN, K.;SHENOY, S. J.;SEN, H. G.;DEB, B. N., INDIAN J. PHARM. SCI., 48,(1986) N 5, 125-132
  作者：NAGARAJAN, K.、SHENOY, S. J.、SEN, H. G.、DEB, B. N.

  DOI：——

  日期：——