7-cyanonaphthalene-2-carboxylic acid | 5043-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-cyanonaphthalene-2-carboxylic acid
• 英文别名: 7-cyano-2-naphthoic acid；7-cyano-[2]naphthoic acid；7-Cyan-[2]naphthoesaeure；7-cyano-2-naphthalenecarboxylic acid
• CAS: 5043-08-3
• 化学式: C₁₂H₇NO₂
• 分子量: 197.193
• InChiKey: QDGDSTIWXLBLNR-UHFFFAOYSA-N

物化性质

• 熔点：
  286-288 °C
• 沸点：
  414.7±20.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 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：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-cyanonaphthalene-2-carboxylic acid 在 盐酸 、 4 A molecular sieve 、 二苯基膦叠氮化物 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 反应 15.5h， 生成 7-aminonaphthalene-2-carbonitrile hydrochloride
  参考文献：
  名称：

  Design, synthesis and biological activity of YM-60828 derivatives: potent and orally-Bioavailable factor Xa inhibitors based on naphthoanilide and naphthalensulfonanilide templates

  摘要：

  Factor Xa (FXa) is a serine protease which plays a pivotal role in the coagulation cascade. The inhibition of FXa has received great interest as a potential target for the development of new antithrombotic drug. Herein we describe a series of novel 7-arnidino-2-naphthoanilide and 7-amidino-2-naphthalensulfonanilide derivatives which are potent FXa inhibitors. These scaffolds are rigid and are allowed to adopt an L-shape conformation which was estimated as the active conformation based on a docking study of YM-60828 with FXa. Optimization of the side chain at the central aniline nitrogen of 7-amidino-2-naphthoanilide has led to several potent and orally active FXa inhibitors. 5h (YM-169964), the best compound of these series, showed potent FXa inhibitory activity (IC50 = 3.9 nM) and effectively prolonged prothrombin time by 9.6-fold ex vivo Lit an oral dose of 3 mg/kg in squirrel monkeys. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00106-2
• 作为产物：
  描述：

  7-cyanonaphthalene-2-carboxylic acid methyl ester 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 15.0h， 以99%的产率得到7-cyanonaphthalene-2-carboxylic acid
  参考文献：
  名称：

  Hypoxia-Activated Prodrugs: Substituent Effects on the Properties of Nitro seco-1,2,9,9a-Tetrahydrocyclopropa[c]benz[e]indol-4-one (nitroCBI) Prodrugs of DNA Minor Groove Alkylating Agents

  摘要：

  Nitrochloromethylbenzindolines (nitroCBIs) are a new class of hypoxia-activated prodrugs for antitumor therapy. The recently reported prototypes undergo hypoxia-selective metabolism to form potent DNA minor groove alkylating agents and are selectively toxic to some but not all hypoxic tumor cell lines. Here we report a series of 31 analogues that bear an extra electron-withdrawing substituent that serves to raise the one-electron reduction potential of the nitroCBI. We identify a subset of compounds, those with a basic side chain and sulfonamide or carboxamide substituent, that have consistently high hypoxic selectivity. The best of these, with a 7-sulfonamide substituent, displays hypoxic cytotoxicity ratios of 275 and 330 in Skov3 and HT29 human tumor cell lines, respectively. This compound (28) is efficiently and selectively metabolized to the corresponding aminoCBI, is selectively cytotoxic tinder hypoxia in all 11 cell lines examined, and demonstrates activity against hypoxic tumor cells in a human tumor xenograft in vivo.

  DOI：

  10.1021/jm901202b

文献信息

• NK1 and NK2-antagonists and compositions and methods of using the same
  申请人：Antel Jochen

  公开号：US20070149537A1

  公开（公告）日：2007-06-28

  3-cyanonaphthalene-1-carboxylic acid perhydroxyalkylmethyl-piperazine compounds of formula I which are antagonistic to tachykinin receptors, pharmaceutical compositions containing such compounds, methods of using such compounds for the treatment and/or inhibition of various diseases and disorders, processes for preparing such piperazine compounds, and intermediate products of these processes.

  3-氰基萘-1-羧酸过羟基烷基甲基哌嗪化合物，其具有对速激肽受体的拮抗作用，包含该化合物的药物组合物，使用该化合物治疗和/或抑制各种疾病和失调的方法，制备这类哌嗪化合物的方法，以及这些过程的中间产品。
• Amidinonaphthyl derivative or salt thereof
  申请人：Yamanouchi Pharmaceutical Co. Ltd

  公开号：US05869501A1

  公开（公告）日：1999-02-09

  An amidinonaphthyl derivative represented by the following general formula (I) which has coagulation factor X inhibiting action and is useful as an anti-thrombus agent and the like, a salt thereof, an intermediate thereof and a pharmaceutical composition which comprises the amidinonaphthyl derivative. An amidinonaphthyl derivative represented by the following general formula (I) or a pharmaceutically acceptable salt thereof. ##STR1## (symbols in the formula have the following meanings; R.sup.1 : a hydrogen atom or a group represented by the formula --A--W--R.sup.4, A: a group represented by the formula ##STR2## a group represented by the formula ##STR3## or a group represented by the formula --SO.sub.2 --, X: an oxygen atom or a sulfur atom, W: a single bond or a group represented by the formula --NR.sup.5 --, R.sup.4 : a hydroxyl group, a lower alkoxy group, etc., R.sup.5 : a hydrogen atom, a carbamoyl group, a lower alkoxycarbonyl group, etc., R.sup.2 : a lower alkyl group, R.sup.3 : a hydrogen atom, a halogen atom, a carboxyl group, B: a lower alkylene group or a carbonyl group, and n: 0 or 1).

  以下是由下列通式（I）表示的酰胺基萘衍生物，具有凝血因子X抑制作用，可用作抗血栓剂等，其盐，中间体以及包括该酰胺基萘衍生物的药物组成物。由下列通式（I）或其药学上可接受的盐表示的酰胺基萘衍生物。 ##STR1## （式中符号的含义如下：R1：氢原子或由公式--A--W--R4表示的基团，A：由公式表示的基团##STR2##由公式表示的基团##STR3##或由公式--SO.sub.2--表示的基团，X：氧原子或硫原子，W：单键或由公式--NR5--表示的基团，R4：羟基，低级烷氧基等，R5：氢原子，氨基甲酰基，低级烷氧羰基基团等，R2：低级烷基，R3：氢原子，卤原子，羧基，B：低级烷基撑或羰基基团，n：0或1）。
• Spiro '1-azabicyclo' 2.2.2! octan-3,5'-oxazolidin - 2'-one! derivatives with affinity to the alpha7 nicotinic acetylcholine receptor
  申请人：Chang Hui-Fang

  公开号：US20060154945A1

  公开（公告）日：2006-07-13

  Compounds of formula I: and pharmaceutically-acceptable salts thereof, wherein Q, Ar 1 , A and Ar 2 are as defined in the specification, pharmaceutical compositions and formulations containing them, methods of using them to treat diseases and conditions either alone or in combination with other therapeutically-active compounds or substances, processes and intermediates used to prepare them, uses of them as medicaments for therapy, uses of them in the manufacture of medicaments and uses of them for diagnostic and analytic purposes.

  公式I的化合物及其药用可接受盐，其中Q、Ar1、A和Ar2的定义如规范中所述，包含它们的药物组合物和制剂，使用它们单独或与其他治疗活性化合物或物质联合治疗疾病和症状的方法，用于制备它们的过程和中间体，将它们用于治疗的药物用途，将它们用于制造药物的用途以及将它们用于诊断和分析目的的用途。
• Nitrobenzindoles and Their use in Cancer Therapy
  申请人：Denny William Alexander

  公开号：US20080119442A1

  公开（公告）日：2008-05-22

  The present invention relates generally to nitro-1,2-dihydro-3H-benzo[e]indoles and related analogues, to their preparation, and to their use as hypoxia-selective drugs and radiosensitizers for cancer therapy, both alone or in combination with radiation and/or other anticancer drugs.

  本发明涉及硝基-1,2-二氢-3H-苯并[e]吲哚及其相关类似物，其制备方法以及其作为低氧选择性药物和放射增敏剂在癌症治疗中的使用，可以单独使用或与辐射和/或其他抗癌药物联合使用。
• Nitrobenzindoles and their use in cancer therapy
  申请人：Auckland Uniservices Limited

  公开号：US07718688B2

  公开（公告）日：2010-05-18

  The present invention relates generally to nitro-1,2-dihydro-3H-benzo[e]indoles and related analogues, to their preparation, and to their use as hypoxia-selective drugs and radiosensitizers for cancer therapy, both alone or in combination with radiation and/or other anticancer drugs.

  本发明涉及硝基-1,2-二氢-3H-苯并[e]吲哚及其相关类似物，其制备方法以及它们作为治疗癌症的低氧选择性药物和放射增敏剂的用途，无论是单独使用还是与放射线和/或其他抗癌药物联合使用。