N-(4-phenylbutyl)acrylamide

• 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: N-(4-phenylbutyl)acrylamide
• 英文别名: N-(4-phenylbutyl)prop-2-enamide
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: BXOCWPZZROGGBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(cyclopropylmethyl)northebaine 、 N-(4-phenylbutyl)acrylamide 以 various solvent(s) 为溶剂， 生成
  参考文献：
  名称：

  Drug design and synthesis of ε opioid receptor agonist: 17-(cyclopropylmethyl)-4,5α-epoxy-3,6β-dihydroxy-6,14-endoethenomorphinan-7α-(N-methyl-N-phenethyl)carboxamide (TAN-821) inducing antinociception mediated by putative ε opioid receptor

  摘要：

  Here we report the new drug design and synthesis of a series of 6,14-endoethenomorphinan-7-carboxamide derivatives as a putative E: opioid receptor agonist. One of these compounds, 17-(cyclopropylmethyl)-4,5alpha-epoxy-3,6beta-dihydroxy-6,14-endoethenomorphinan-7alpha-(N-methyl-N-phenethyl)carboxamide (TAN-821), showed agonistic activity for a putative E opioid receptor (IC50 = 71.71 nM) in the rat vas deferens (RVD) preparations. TAN-821 stimulated the binding of the nonhydrolyzable guanosine 5'-triphosphate analog, guanosine 5'-(gamma-thio)-triphosphate (GTPgammaS), to the mouse pons/medulla membrane via the activation of putative E: opioid receptor. Moreover, TAN-821 given intracerbroventricularly (i.c.v.) produced a marked antinociception in the tail-flick test (ED50 = 1.73 mug) and the hot-plate test (ED50 = 2.05 mug) in a dose-dependent manner. The antinociception induced by TAN-821 administered i.c.v. was blocked by the i.c.v.-pretreatment with a putative epsilon opioid receptor partial agonist beta-endorphin [1-27], but not a mu opioid receptor antagonist beta-FNA, a delta opioid receptor antagonist NTI, or a kappa opioid receptor antagonist nor-BNI. The present results suggest that TAN-821 may be a useful tool for the investigation on the pharmacological properties of the putative epsilon opioid receptor. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.024

文献信息

• Morphinane derivatives and medicinal use thereof
  申请人：Toray Industries, Inc.

  公开号：US06187782B1

  公开（公告）日：2001-02-13

  Novel morphinan derivatives and pharmaceutically acceptable acid addition salts thereof as compounds having abilities to bind to opioid &egr;-receptor, which have agonist or antagonist activities, are disclosed. The morphinan derivatives according to the present invention are represented by the formula (I).

  本发明涉及一种新型吗啡样化合物及其药学上可接受的酸盐，可作为与μ-阿片受体结合的化合物，具有激动剂或拮抗剂活性。根据本发明，所述吗啡样化合物的衍生物由式(I)表示。
• MORPHINANE DERIVATIVES AND MEDICINAL USE THEREOF
  申请人：TORAY INDUSTRIES, INC.

  公开号：EP0915094A1

  公开（公告）日：1999-05-12

  Novel morphinan derivatives and pharmaceutically acceptable acid addition salts thereof as compounds having abilities to bind to opioid ε-receptor, which have agonist or antagonist activities, are disclosed. The morphinan derivatives according to the present invention are represented by the formula (I).

  本发明公开了新型吗啡南衍生物及其药学上可接受的酸加成盐，这些化合物具有与阿片ε受体结合的能力，具有激动剂或拮抗剂活性。根据本发明的吗啡南衍生物由式(I)表示。
• EP1482983A4
  申请人：——

  公开号：EP1482983A4

  公开（公告）日：2006-07-12
• NON-MYELOABLATIVE TOLEROGENIC TREATMENT WITH TYRPHOSTINS
  申请人：YISSUM RESEARCH DEVELOPMENT COMPANYOF THE HEBREW UNIVERSITY OF JERUSALEM

  公开号：EP1482983A2

  公开（公告）日：2004-12-08
• COMBINATION THERAPIES
  申请人：Mirati Therapeutics, Inc.

  公开号：EP3849538A1

  公开（公告）日：2021-07-21