4-碘萘-1-羧酸 | 91059-41-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-碘萘-1-羧酸
• 英文名称: 4-Iod-naphthoesaeure-(1)
• 英文别名: 4-Iodonaphthalene-1-carboxylic acid
• CAS: 91059-41-5
• 化学式: C₁₁H₇IO₂
• 分子量: 298.08
• InChiKey: IKUGXOILLMFCRF-UHFFFAOYSA-N

物化性质

• 熔点：
  208-209 °C
• 沸点：
  424.2±28.0 °C(Predicted)
• 密度：
  1.884±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-碘萘-1-羧酸 在 氯化亚砜 作用下， 反应 2.0h， 生成 4-iodo-1-naphthoyl chloride
  参考文献：
  名称：

  Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: Steric and electronic effects of 4- and 8-halogenated naphthoyl substituents

  摘要：

  To develop SAR at both the cannabinoid CB1 and CB2 receptors for 3-(1-naphthoyl)indoles bearing moderately electron withdrawing substituents at C-4 of the naphthoyl moiety, 1-propyl and 1-pentyl-3-(4-fluoro, chloro, bromo and iodo-1-naphthoyl) derivatives were prepared. To study the steric and electronic effects of substituents at the 8-position of the naphthoyl group, the 3-(4-chloro, bromo and iodo-1-naphthoyl) indoles were also synthesized. The affinities of both groups of compounds for the CB1 and CB2 receptors were determined and several of them were evaluated in vivo in the mouse. The effects of these substituents on receptor affinities and in vivo activity are discussed and structure-activity relationships are presented. Although many of these compounds are selective for the CB2 receptor, only three JWH-423, 1-propyl-3-(4-iodo-1-naphthoyl)indole, JWH-422, 2-methyl-1-propyl-3-(4-iodo-1-naphthoyl) indole, the 2-methyl analog of JWH-423 and JWH-417, 1-pentyl-3-(8-iodo-1-naphthoyl)indole, possess the desirable combination of low CB1 affinity and good CB2 affinity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.038
• 作为产物：
  描述：

  4-氨基-1-萘羧腈 在 盐酸 、 水 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 4.0h， 生成 4-碘萘-1-羧酸
  参考文献：
  名称：

  [EN] THERAPEUTIC COMPOUNDS: PYRIDINE AS SCAFFOLD
  [FR] COMPOSES THERAPEUTIQUES DANS LESQUELS LA PYRIDINE EST UTILISEE COMME SQUELETTE

  摘要：

  其中A、A1、A2、A3、A4、R2、R3、R4和n的化合物的公式I、IA和IB或IC或其药学上可接受的盐：其中A、A1、A2、A3、A4、R2、R3、R4和n的定义如规范中所述，以及包括这些化合物的盐和药物组合物已经准备好。它们在治疗中很有用，特别是在疼痛管理中。

  公开号：

  WO2005115986A1

文献信息

• Therapeutic Compounds: Pyridine as Scaffold
  申请人：Amin Kosrat

  公开号：US20070225292A1

  公开（公告）日：2007-09-27

  Compounds of formula I or pharmaceutically acceptable salts thereof: wherein R 1 , R 2 , R 3 , R 4 , n and A are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

  式I的化合物或其药学上可接受的盐：其中R1，R2，R3，R4，n和A的定义如规范中所述，以及包括该化合物的盐和制备的药物组合物。它们在治疗中有用，特别是在疼痛管理方面。
• Synthèse de l'acide 4-iodo-1-naphtoïque
  作者：Henri Goldstein、Rolf Mohr、Theodor Blezinger

  DOI：10.1002/hlca.193501801110

  日期：——
• Design, synthesis, and in vitro evaluation of new naphthylnitrobutadienes with potential antiproliferative activity: Toward a structure/activity correlation
  作者：Giovanni Petrillo、Maria A. Mariggiò、Cinzia Aiello、Cinzia Cordazzo、Carla Fenoglio、Stefano Morganti、Michela Croce、Egon Rizzato、Domenico Spinelli、Massimo Maccagno、Lara Bianchi、Claudia Prevosto、Cinzia Tavani、Maurizio Viale

  DOI：10.1016/j.bmc.2007.09.042

  日期：2008.1

  On the grounds of previous encouraging results on the antitumor activity of (1E,3E)-1,4-bis(1-naphthyl)-2,3-dinitro-1, 3-butadiene (1), we have designed and synthesized two new molecules [(1E,3E)-1,4-bis(4-carboxy-1-naphthyl)-2,3-dinitro-1,3-butadiene (2) and methyl (2Z,4E)-2-methylsulfanyl-5-(1-naphthyl)-4-nitro-2,4-pentadienoate (3)] characterized by a common naphthyl-nitrobutadiene array but with different structural properties, with the aim of approaching to some structure-activity correlation. When 2 and 3 were analyzed in vitro for their inhibition of cell proliferation and pro-apoptotic properties, the carboxyderivative 2 did not furnish appreciable results. In contrast, 3 (which contains only one of the two naphthyinitroethenyl moieties of the original compound 1) showed remarkable activities in the range of micromolar concentrations (in six over eight cell lines its IC(50)s are in the 1-3 mu M range), with a significant improvement compared to 1. In particular, 3 proved able to bind to DNA, to upregulate p53, to block cells in the G2/M phase of their cycle, and to induce apoptosis. Thus, very interestingly, the performance of 3 with respect to 1 shows that a single 1-(1-naphthyl)-2-nitroethene moiety is able to ensure better (on four out of eight of the cell lines tested) or comparable levels of activity. This result suggests that the 'molecular-simplification strategy' could furnish a useful instrument for future design in our antitumor research. (C) 2007 Elsevier Ltd. All rights reserved.
• THERAPEUTIC COMPOUNDS: PYRIDINE AS SCAFFOLD
  申请人：AstraZeneca AB

  公开号：EP1756060A1

  公开（公告）日：2007-02-28
• [EN] THERAPEUTIC COMPOUNDS: PYRIDINE AS SCAFFOLD<br/>[FR] COMPOSES THERAPEUTIQUES DANS LESQUELS LA PYRIDINE EST UTILISEE COMME SQUELETTE
  申请人：ASTRAZENECA AB

  公开号：WO2005115986A1

  公开（公告）日：2005-12-08

  Compounds of formulas I, IA, and IB or IC or pharmaceutically acceptable salts thereof: wherein A, A1, A2, A3, A4, R2, R3, R4 and n are as defined in the specifications well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

  其中A、A1、A2、A3、A4、R2、R3、R4和n的化合物的公式I、IA和IB或IC或其药学上可接受的盐：其中A、A1、A2、A3、A4、R2、R3、R4和n的定义如规范中所述，以及包括这些化合物的盐和药物组合物已经准备好。它们在治疗中很有用，特别是在疼痛管理中。