3-溴-N-环己基丙酰胺 | 33257-32-8

• 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
• 中文名称: 3-溴-N-环己基丙酰胺
• 英文名称: 3-bromo-N-cyclohexylpropanamide
• 英文别名: 3-bromo-propionic acid cyclohexylamide；3-Brom-propionsaeure-cyclohexylamid；3-bromo-N-cyclohexylpropionamide；N-Cyclohexyl-β-brom-propionsaeureamid
• CAS: 33257-32-8
• 化学式: C₉H₁₆BrNO
• mdl: MFCD05839329
• 分子量: 234.136
• InChiKey: PHWGXHKYNXZVIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.888
• 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：

  3-溴-N-环己基丙酰胺 在 sodium hydride 作用下， 生成 N-环己基丙-2-烯酰胺
  参考文献：
  名称：

  The synthesis of β-lactams by the cyclization of β-halopropionamides

  摘要：

  DOI：

  10.1016/s0040-4039(01)85997-9
• 作为产物：
  描述：

  环己胺 、 3-溴丙酰氯 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 3-溴-N-环己基丙酰胺
  参考文献：
  名称：

  分子内氮杂-Prins型反应合成嘧啶并[2,1-a]异吲哚酮和异吲哚并[2,1-a]喹唑啉酮

  摘要：

  涉及一种新颖氮杂普林斯型环化反应Ñ -acyliminium离子和酰胺被报告四氢嘧啶并[2,1-的合成一个]异吲哚-2,6-二酮和6,6-一个-dihydroisoindolo [2,1-一个]喹唑啉-5,11-二酮衍生物，产率极好。该策略的特点是试剂价格低廉，反应条件温和，N-杂环骨架的无金属合成。此外，合成后的修饰导致其前所未有的三唑、四环二氮杂环戊二烯[ def ]菲-1,4(9 a 1 H )-二酮和羰基衍生物的形成。

  DOI：

  10.1039/d1cc04554g

文献信息

• Synthesis of pyrimido[2,1-<i>a</i>]isoindolone and isoindolo[2,1-<i>a</i>]quinazolinone <i>via</i> intramolecular aza-Prins type reaction
  作者：Subhamoy Biswas、Bikoshita Porashar、Pallav Jyoti Arandhara、Anil K. Saikia

  DOI：10.1039/d1cc04554g

  日期：——

  A novel aza-Prins type cyclization reaction involving N-acyliminium ions and amides is reported for the synthesis of tetrahydropyrimido[2,1-a]isoindole-2,6-dione and 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives in excellent yields. The strategy features inexpensive reagents, mild reaction conditions, and metal-free synthesis of N-heterocyclic frameworks. Further, post-synthetic modification

  涉及一种新颖氮杂普林斯型环化反应Ñ -acyliminium离子和酰胺被报告四氢嘧啶并[2,1-的合成一个]异吲哚-2,6-二酮和6,6-一个-dihydroisoindolo [2,1-一个]喹唑啉-5,11-二酮衍生物，产率极好。该策略的特点是试剂价格低廉，反应条件温和，N-杂环骨架的无金属合成。此外，合成后的修饰导致其前所未有的三唑、四环二氮杂环戊二烯[ def ]菲-1,4(9 a 1 H )-二酮和羰基衍生物的形成。
• Synthesis and Structure-Activity Relationships of LP1 Derivatives: N-Methyl-N-phenylethylamino Analogues as Novel MOR Agonists
  作者：Rita Turnaturi、Carmela Parenti、Orazio Prezzavento、Agostino Marrazzo、Paschalina Pallaki、Zafiroula Georgoussi、Emanuele Amata、Lorella Pasquinucci

  DOI：10.3390/molecules23030677

  日期：——

  lower efficacy than LP1. Moreover, in a mouse model of acute thermal nociception, compound 5c, intraperitoneally administered, exhibits naloxone-reversed antinociceptive properties with an ED50 of 4.33 mg/kg. These results expand our understanding of the importance of N-substituent structural variations in the opioid receptor profile of cis-(−)-N-normetazocine derivatives and identify a new MOR agonist

  cis-(-)-N-normetazocine 衍生物的阿片类药物药理学特征深受其 N 取代基性质的影响。在这里，我们的工作重点是先导 LP1 的新型衍生物的合成和药理学评价，LP1 是一种多靶点阿片类镇痛化合物，具有 N-苯基丙酰胺取代基。LP1 衍生物 5a-d 和 6a-d 的特征在于 N-取代基上的灵活基团，使它们能够相对于顺-(-)-N-去甲甲佐辛核重新定位，从而在 mu、delta 和 kappa 产生不同的药理学特征阿片受体（MOR、DOR 和 KOR）在体外和体内试验中。在该系列中，具有最佳体外和体内特性的化合物 5c 产生了一种 MOR 激动剂，在竞争性结合测定中其 KiMOR 为 6.1 nM，IC50 值为 11。在稳定表达 MOR 的 HEK293 细胞中测量 cAMP 积累时，5 nM 和 72% 的 Imax，其功效略低于 LP1。此外，在急性热伤害感受的小鼠模型中，腹膜内给药的化合物
• Substituted heterocyclic compounds
  申请人：——

  公开号：US20040152890A1

  公开（公告）日：2004-08-05

  Disclosed are novel heterocyclic derivatives, useful for the treatment of various disease states, in particular cardiovascular diseases such as atrial and ventricular arrhythmias, intermittent claudication, Prinzmetal's (variant) angina, stable and unstable angina, exercise induced angina, congestive heart disease, and myocardial infarction. The compounds are also useful in the treatment of diabetes.

  本发明涉及新型杂环衍生物，可用于治疗各种疾病状态，特别是心血管疾病，如心房和心室心律失常、间歇性跛行、普林兹梅特尔（变异型）心绞痛、稳定和不稳定性心绞痛、运动诱发性心绞痛、充血性心力衰竭和心肌梗塞。该化合物也可用于糖尿病的治疗。
• Substituted piperazine compounds and their use as fatty acid oxidation inhibitors
  申请人：CV THERAPEUTICS, INC.

  公开号：EP1806346A1

  公开（公告）日：2007-07-11

  Disclosed are novel heterocyclic derivatives, useful for the treatment of various disease states, in particular cardiovascular diseases such as atrial and ventricular arrhythmias, intermittent claudication, Prinzmetal's (variant) angina, stable and unstable angina, exercise induced angina, congestive heart disease, and myocardial infarction. The compounds are also useful in the treatment of diabetes.

  所公开的新型杂环衍生物可用于治疗各种疾病，尤其是心血管疾病，如房性和室性心律失常、间歇性跛行、普林兹梅塔尔（变异型）心绞痛、稳定型和不稳定型心绞痛、运动诱发心绞痛、充血性心脏病和心肌梗塞。这些化合物还可用于治疗糖尿病。
• Evaluation of N-substitution in 6,7-benzomorphan compounds
  作者：Lorella Pasquinucci、Orazio Prezzavento、Agostino Marrazzo、Emanuele Amata、Simone Ronsisvalle、Zafiroula Georgoussi、Danai-Dionysia Fourla、Giovanna M. Scoto、Carmela Parenti、Giuseppina Aricò、Giuseppe Ronsisvalle

  DOI：10.1016/j.bmc.2010.06.005

  日期：2010.7

  6,7-Benzomorphan derivatives, exhibiting different mu, delta, and kappa receptor selectivity profiles depending on the N-substituent, represent a useful skeleton for the synthesis of new and better analgesic agents. In this work, an aromatic ring and/or alkyl residues have been used with an N-propanamide or N-acetamide spacer for the synthesis of a new series of 5,9-dimethyl-2'-hydroxy-6,7-benzomorphan derivatives (12-22). Data obtained by competition binding assays showed that the mu opioid receptor seems to prefer an interaction with the 6,7-benzomorphan ligands having an N-substituent with a propanamide spacer and less hindered amide. Highly stringent features are required for delta receptor interaction, while an N-acetamide spacer and/or bulkier amide could preferentially lead to kappa receptor selectivity. In the propanamide series, compound 12 (named LP1) displayed high mu affinity (K(i) = 0.83 nM), good delta affinity (K(i) = 29 nM) and low affinity for the kappa receptor (K(i) = 110 nM), with a selectivity ratio delta/mu and kappa/mu of 35.1 and 132.5, respectively. Further, in the adenylyl cyclase assay, LP1 displayed a mu/delta agonist profile, with IC(50) values of 4.8 and 12 nM at the mu and delta receptors, respectively. The antinociceptive potency of LP1 in the tail-flick test after sc administration in rat was comparable with the potency of morphine (ED(50) = 2.03 and 2.7 mg/kg, respectively), and was totally reversed by naloxone. LP1, possessing a mu/delta agonist profile, could represent a lead in further developing benzomorphan-based ligands with potent in vivo analgesic activity and a reduced tendency to induce side effects. (C) 2010 Elsevier Ltd. All rights reserved.