4-butyl-1-naphthoic acid | 108122-90-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-butyl-1-naphthoic acid
• 英文别名: 4-Butyl-[1]naphthoesaeure；4-butylnaphthalene-1-carboxylic acid
• CAS: 108122-90-3
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: IDIKCXJPQWTKAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  4-butyl-1-naphthoic acid 在 氯化亚砜 、 二氯乙基铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 96.25h， 生成 (4-丁基萘-1-基)-(1-丙基吲哚-3-基)甲酮
  参考文献：
  名称：

  Structure–activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB1 and CB2 receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB2 receptor agonists

  摘要：

  In an effort to improve indole-based CB2 cannabinoid receptor ligands and also to develop SAR for both the CB1 and CB2 receptors, 47 indole derivatives were prepared and their CB1 and CB2 receptor affinities were determined. The indole derivatives include 1-propyl- and 1-pentyl-3-(1-naphthoyl)indoles both with and without a 2-methyl substituent. Naphthoyl substituents include 4- and 7-alkyl groups as well as 2-, 4-, 6-, 7-methoxy and 4-ethoxy groups. The effects of these substituents on receptor affinities are discussed and structure-activity relationships are presented. In the course of this work three new highly selective CB2 receptor agonists were identified, 1-propyl-3-(4-methyl-1-naphthoylindole (JWH-120), 1-propyl-2-methyl-3-(6-methoxy-1-naphthoylindole (JWH-151), and 1-pentyl-3-(2-methoxy-1-naphthoylindole (JWH-267). GTPgammaS assays indicated that JWH-151 is a full agonist at CB2, while JWH-120 and JWH-267 are partial agonists. Molecular modeling and receptor docking studies were carried out on a set of 3-(4-propyl-1-naphthoyl)indoles, a set of 3-(6-methoxy-1-naphthoyl)indoles and the pair of N-pentyl-3-(2-methoxy-1-naphthoyl)indoles. Docking studies indicated that the CB1 receptor affinities of these compounds were consistent with their aromatic stacking interactions in the aromatic microdomain of the CB1 receptor. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.050
• 作为产物：
  描述：

  1-丁基-4-氯甲基-萘 在 氢氧化钾 、 potassium permanganate 作用下， 生成 4-butyl-1-naphthoic acid
  参考文献：
  名称：

  Sergiewskaja; Safonowa, Zhurnal Obshchei Khimii, 1957, vol. 27, p. 1645,1647; engl. Ausg. S. 1715, 1717

  摘要：

  DOI：

文献信息

• CB2-selective cannabinoid analogues
  申请人：Martin R. Billy

  公开号：US20050009903A1

  公开（公告）日：2005-01-13

  Cannabinoid analogues that exhibit specificity for the CB 2 cannabinoid receptor are provided. The analogues are 1-methoxy-, 1-deoxy-11-hydroxy- and 11-hydroxy-1-methoxy-Δ 8 -tetrahydrocannabinols and 1-alkyl-3(1-naphthoyl)indoles. The compounds are useful for the treatment of pain (especially pain resulting from inflammation) and cancer (especially glioma tumors).

  提供了对CB2大麻素受体具有特异性的大麻素类似物。这些类似物是1-甲氧基-、1-去氧-11-羟基-和11-羟基-1-甲氧基-Δ8-四氢大麻酚以及1-烷基-3(1-萘酰)吲哚。这些化合物对于治疗疼痛（尤其是由炎症引起的疼痛）和癌症（尤其是胶质瘤）具有用途。
• Synthesis and characterization of 3-aminoquinoline derivatives and studies of photophysicochemical behaviour and antimicrobial activities
  作者：Gulay Zengin、Ali Muayad Nafea Al Kawaz、Huseyin Zengin、Adem Mert、Bedia Kucuk

  DOI：10.1016/j.molstruc.2015.09.016

  日期：2016.1

  Photoluminescence (PL). The quinoline ring core, typical of aminoquinolines, and a naphthalene group was combined to devise (4-alkyl-1-naphthyl)-quinolin-3-ylamide derivatives. These derivatives were designed and synthesized in light of the chemical and biological profiles of these important subunits. All the compounds were evaluated for their in vitro antibacterial and antifungal activities by the paper disc

  摘要 合成了一系列 3-氨基喹啉衍生物，并通过元素分析、核磁共振（ 1 H 和 13 C NMR）、液相色谱-质谱（LC）等多种分析技术确认了其化学结构。 -MS-MS)、紫外-可见光谱 (UV-Vis)、傅立叶变换红外光谱 (FTIR) 和光致发光 (PL)。喹啉环核心（典型的氨基喹啉）和萘基团结合以设计（4-烷基-1-萘基）-喹啉-3-基酰胺衍生物。这些衍生物是根据这些重要亚基的化学和生物学特征设计和合成的。所有化合物的体外抗菌和抗真菌活性通过纸盘扩散法与革兰氏阳性枯草芽孢杆菌进行评估，巨大芽孢杆菌和金黄色葡萄球菌、革兰氏阴性产气肠杆菌、大肠杆菌、肺炎克雷伯菌和铜绿假单胞菌以及白色念珠菌、酿酒酵母和解脂耶氏酵母。这些化合物对革兰氏阳性菌和革兰氏阴性菌以及几种酵母菌显示出抗菌活性，因此它们的活性不限于任何特定类型的微生物。
• Synthesis and characterization of cannabimimetic aminoalkylindole based 5-(4-alkyl-1-naphthoylamino)-1,3,4-thiadiazole-2-sulfonamides
  作者：Gulay Zengin、Zehra Nalbantbasi、Huseyin Zengin、Hasan Turkmen

  DOI：10.1002/hc.20738

  日期：2011.11

  A novel series of cannabimimetic aminoalkylindole-based sulfonamide derivatives was synthesized. These new compounds were synthesized by reacting acyl chlorides of naphthoic acids with deacetylated acetazolamide in the presence of N-ethyl-morpholine to give structures incorporating 1-naphthoyl groups of cannabimimetic aminoalkylindoles and a five-membered heteroring typical of antiglaucoma sulfa drugs

  合成了一系列新型大麻素氨基烷基吲哚基磺酰胺衍生物。这些新化合物是通过在 N-乙基-吗啉的存在下使萘甲酸的酰氯与脱乙酰乙酰唑胺反应来合成的，从而得到包含 1-萘甲酰基的大麻模拟氨基烷基吲哚和抗青光眼磺胺类药物典型的五元杂环的结构。使用标准技术表征合成的化合物。还研究了这些衍生物的光致发光，其中对位芳环上更多的给电子基团导致主峰强度增加并转移到更高的发射波长。© 2011 Wiley Periodicals, Inc. 杂原子化学 22:707–714, 2011; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.20738
• Zengin, Gulay; Mert, Adem; Zengin, Huseyin, Indian Journal of Heterocyclic Chemistry, 2017, vol. 27, # 1, p. 1 - 11
  作者：Zengin, Gulay、Mert, Adem、Zengin, Huseyin

  DOI：——

  日期：——
• Structure–activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB1 and CB2 receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB2 receptor agonists
  作者：John W. Huffman、Gulay Zengin、Ming-Jung Wu、Jianzhong Lu、George Hynd、Kristen Bushell、Alicia L.S. Thompson、Simon Bushell、Cindy Tartal、Dow P. Hurst、Patricia H. Reggio、Dana E. Selley、Michael P. Cassidy、Jenny L. Wiley、Billy R. Martin

  DOI：10.1016/j.bmc.2004.09.050

  日期：2005.1

  In an effort to improve indole-based CB2 cannabinoid receptor ligands and also to develop SAR for both the CB1 and CB2 receptors, 47 indole derivatives were prepared and their CB1 and CB2 receptor affinities were determined. The indole derivatives include 1-propyl- and 1-pentyl-3-(1-naphthoyl)indoles both with and without a 2-methyl substituent. Naphthoyl substituents include 4- and 7-alkyl groups as well as 2-, 4-, 6-, 7-methoxy and 4-ethoxy groups. The effects of these substituents on receptor affinities are discussed and structure-activity relationships are presented. In the course of this work three new highly selective CB2 receptor agonists were identified, 1-propyl-3-(4-methyl-1-naphthoylindole (JWH-120), 1-propyl-2-methyl-3-(6-methoxy-1-naphthoylindole (JWH-151), and 1-pentyl-3-(2-methoxy-1-naphthoylindole (JWH-267). GTPgammaS assays indicated that JWH-151 is a full agonist at CB2, while JWH-120 and JWH-267 are partial agonists. Molecular modeling and receptor docking studies were carried out on a set of 3-(4-propyl-1-naphthoyl)indoles, a set of 3-(6-methoxy-1-naphthoyl)indoles and the pair of N-pentyl-3-(2-methoxy-1-naphthoyl)indoles. Docking studies indicated that the CB1 receptor affinities of these compounds were consistent with their aromatic stacking interactions in the aromatic microdomain of the CB1 receptor. (C) 2004 Elsevier Ltd. All rights reserved.