2-Methoxy-3-cyano-1-naphthoyl Chloride | 263388-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Methoxy-3-cyano-1-naphthoyl Chloride
• 英文别名: 3-cyano-2-methoxy-1-naphthalenecarbonyl chloride；3-cyano-2-methoxy-1-naphthoyl chloride；3-cyano-2-methoxynaphthalene-1-carbonyl chloride
• CAS: 263388-13-2
• 化学式: C₁₃H₈ClNO₂
• 分子量: 245.665
• InChiKey: ZEIKSACPSHZQQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Methoxy-3-cyano-1-naphthoyl Chloride 在 重铬酸吡啶 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.83h， 生成 N-[2-(S)-(3,4-dichlorophenyl)-3-aminocarbonylpropyl]-N-methyl-3-cyano-2-methoxy-1-naphthamide
  参考文献：
  名称：

  Structural Analysis and Optimization of NK₁ Receptor Antagonists through Modulation of Atropisomer Interconversion Properties

  摘要：

  We have previously described a series of antagonists that showed high potency and selectivity for the NK1 receptor. However, these compounds also had the undesirable property of existing as a mixture of interconverting rotational isomers. Here we show that alteration of the 2-naphthyl substituent can modulate the rate of isomer exchange. Comparisons of the NK1 receptor affinity for the various conformational. forms has facilitated the development of a detailed NK1 pharmacophore model.

  DOI：

  10.1021/jm030197g
• 作为产物：
  描述：

  2-甲氧基-3-氰基-1-萘酸甲酯 在 lithium hydroxide 、 草酰氯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 2-Methoxy-3-cyano-1-naphthoyl Chloride
  参考文献：
  名称：

  Design, Synthesis, and SAR of Tachykinin Antagonists:  Modulation of Balance in NK₁/NK₂ Receptor Antagonist Activity

  摘要：

  Through optimization of compounds based on the dual NK1/NK2 antagonist ZD6021, it was found that alteration of two key regions could modulate the balance of NK1 and NK2 potency. Substitution of the 2-naphthalene position in analogues of ZD6021 resulted in increased NK1 potency and thus afforded NK1 preferential antagonists. Alterations of the piperidine region could then increase NK2 potency to restore dual NK1/NK2 selectivity. Through these efforts, three novel receptor antagonists from a single chemically related series were identified; two are dual NK1/NK2 antagonists, and the third is an NK1 preferential antagonist. In this paper, the factors affecting the balance of NK1 and NK2 selectivity in this series are discussed and the in vitro and in vivo properties of the novel antagonists are described.

  DOI：

  10.1021/jm020094i

文献信息

• [EN] NAPHTHAMIDE DERIVATIVES AND THEIR USE<br/>[FR] DERIVES DE NAPHTAMIDE ET LEUR UTILISATION
  申请人：ASTRAZENECA AB

  公开号：WO2004020411A1

  公开（公告）日：2004-03-11

  Compounds having the following structure wherein R1, R2, R3, R4, m and n are as defined in the specification, in vivo-hydrolysable precursors thereof, pharmaceutically-acceptable salts thereof, the use in therapy and pharmaceutical compositions and methods of treatment using the same.

  具有以下结构的化合物，其中R1、R2、R3、R4、m和n如规范中定义，其体内可水解的前体，其药用可接受的盐，以及在治疗中的使用、制药组合物和使用相同方法的治疗方法。
• Novel n-( 2-phenyl-3-aminopropyl)naphtamides
  申请人：——

  公开号：US20040014809A1

  公开（公告）日：2004-01-22

  A compound of the formula 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , X 1 and X 2 are as defined in the specification useful for the treatment of diseases in which action of the neurokinin 1 receptor is implicated, methods of using such compounds and pharmaceutical compositions comprising such compounds.

  一种化合物的公式如下，其中R1、R2、R3、R4、R5、R6、X1和X2如规范中定义，用于治疗神经激肽1受体作用所涉及的疾病，使用这种化合物的方法以及包含这种化合物的药物组合物。
• N-(2-phenyl-4-amino-butyl)-1-naphthamides as neurokinin-1 receptor antagonists
  申请人：Astrazeneca AB

  公开号：US06476077B1

  公开（公告）日：2002-11-05

  A compound having the general formula (I): R1R2N—CH2CH2—CHAr1—CH2—NR3—CO—R4 wherein: R1 is hydrogen, C1-6 alkyl, C2-6 alkenyl, aryl, C1-6 alkanoyl C1-6 alkoxycarbonyl or arylcarbonyl; any of such groups being optionally substituted; R2 is hydrogen or C1-6 alkyl; or R1 or R2 are joined to form an optionally substituted morpholino ring; Ar1 is phenyl mono- or di-substituted by halo; R3 is hydrogen or C1-6 alkyl; R4 is optionally substituted naphth-1-yl; or pharmaceutically acceptable salts thereof. These compounds antagonize the pharmacological actions of the endogenous neuropeptide tachykinins, particularly the neurokinin 1 (NK1) receptor.

  化合物的一般式为（I）：R1R2N—CH2CH2—CHAr1—CH2—NR3—CO—R4，其中：R1为氢，C1-6烷基，C2-6烯基，芳基，C1-6烷酰基，C1-6烷氧羰基或芳基羰基；这些基团中的任何一个可以选择性地被取代；R2为氢或C1-6烷基；或者R1或R2被结合形成一个可以选择性地被取代的吗啡环；Ar1为苯基，单取代或双取代为卤素；R3为氢或C1-6烷基；R4为可以选择性地被取代的萘-1-基；或其药学上可接受的盐。这些化合物拮抗内源性神经肽tachykinins的药理作用，特别是神经激肽1（NK1）受体。
• Naphthamide neurokinin antagonists for use as medicaments
  申请人：——

  公开号：US20030158180A1

  公开（公告）日：2003-08-21

  A compound having the general formula (Ia) and methods of using such compounds for the treatment of diseases and pharmaceutical composition comprising such compounds.

  一种具有一般式(Ia)的化合物以及使用这种化合物治疗疾病的方法和包含这种化合物的制药组合物。
• Neurokinin antagonists for use as medicaments
  申请人：——

  公开号：US20030158170A1

  公开（公告）日：2003-08-21

  A compound having the general formula (I) and methods of using such compounds for the treatment of diseases and pharmaceutical composition comprising such compounds.

  一种具有通式(I)的化合物，以及使用此类化合物治疗疾病的方法和包含此类化合物的制药组合物。