4-[(2-methyl-4-quinolinyl)methoxy]benzoyl chloride | 362704-62-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-[(2-methyl-4-quinolinyl)methoxy]benzoyl chloride
• 英文别名: 4-(2-methylquinolin-4-ylmethoxy)benzoyl chloride；4-[(2-Methylquinolin-4-yl)methoxy]benzoyl chloride
• CAS: 362704-62-9
• 化学式: C₁₈H₁₄ClNO₂
• 分子量: 311.768
• InChiKey: UTLCDSCDCPIBEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(2-methyl-4-quinolinyl)methoxy]benzoyl chloride 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(2-formylphenyl)-4-[(2-methylquinolin-4-yl)methoxy]benzamide
  参考文献：
  名称：

  Hydantoins, triazolones, and imidazolones as selective non-hydroxamate inhibitors of tumor necrosis factor-α converting enzyme (TACE)

  摘要：

  We have discovered selective and potent inhibitors of TACE that replace the common hydroxamate zinc binding group with a hydantoin, triazolone, and imidazolone heterocycle. These novel heterocyclic inhibitors of a zinc metalloprotease were designed using a pharmacophore model that we previously described while developing hydantoin and pyrimidinetrione (barbiturate) inhibitors of TACE. The potency and binding orientation of these inhibitors is discussed and they are modeled into the X-ray crystal structure of TACE and compared to hydroxamate and earlier hydantoin TACE inhibitors which share the same 4-[(2-methyl-4-quinolinyl)methoxy]benzoyl Pl' group. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.076
• 作为产物：
  描述：

  methyl 4-[(2-methylquinolin-4-yl)methoxy]benzoate 在 lithium hydroxide 、 氯化亚砜 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 4-[(2-methyl-4-quinolinyl)methoxy]benzoyl chloride
  参考文献：
  名称：

  Discovery of low nanomolar non-hydroxamate inhibitors of tumor necrosis factor-α converting enzyme (TACE)

  摘要：

  Using a pyrimidine-2,4,6-trione motif as a zinc-binding group, a series of selective inhibitors of tumor necrosis factor-alpha converting enzyme (TACE) was discovered. Optimization of initial lead I resulted in a potent inhibitor (51), with an IC50 of 2 nM in a porcine TACE assay. To the best of our knowledge, compound 51 and related analogues represent first examples of non-hydroxamate-based inhibitors of TACE with single digit nanomolar potency. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.048

文献信息

• Barbituric acid derivatives as inhibitors of TNF-alpha converting enzyme (TACE) and/or matrix metalloproteinases
  申请人：——

  公开号：US20030229084A1

  公开（公告）日：2003-12-11

  The present application describes novel barbituric acid derivatives of formula I: 1 or pharmaceutically acceptable salt or prodrug forms thereof, wherein A, B, L, R 1 , R 2 , R 3 , R 4 , R 5 , n, W, U, X, Y, Z, U a , X a , Y a , and Z a are defined in the present specification, which are useful as TNF-&agr; converting enzyme (TACE) and matrix metalloproteinases (MMP) inhibitors.

  本申请描述了式I的新型巴比妥酸衍生物： 1 或其药用可接受的盐或前药形式，其中A、B、L、R 1 、R 2 、R 3 、R 4 、R 5 、n、W、U、X、Y、Z、U a 、X a 、Y a 和Z a 在本规范中定义，这些衍生物可用作TNF-α转化酶（TACE）和基质金属蛋白酶（MMP）抑制剂。
• Beta-amino acid derivatives as inhibitors of matrix metalloproteases and TNF-alpha
  申请人：——

  公开号：US20040072802A1

  公开（公告）日：2004-04-15

  The present application describes novel &bgr;-amino acid derivatives of formula I: 1 or pharmaceutically acceptable salt or prodrug forms thereof, wherein A, X, Z, U a , X a , Y a , Z a , R 1 , R 2 , R 3 , R 4 , and R 4a are defined in the present specification, which are useful as metalloprotease and/or as TNF-&agr; inhibitors.

  本申请描述了式I的新颖β-氨基酸衍生物：1或其药用可接受的盐或前药形式，其中A、X、Z、Ua、Xa、Ya、Za、R1、R2、R3、R4和R4a在本规范中有定义，这些衍生物可用作金属蛋白酶和/或TNF-α抑制剂。
• Hydantoins and related heterocycles as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE)
  申请人：——

  公开号：US20030130273A1

  公开（公告）日：2003-07-10

  The present application describes novel hydantoin derivatives of formula (I): 1 or pharmaceutically acceptable salt or prodrug forms thereof, wherein A, B, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 11 , and n are defined in the present specification, which are useful as inhibitors of matrix metalloproteinases (MMP), TNF-&agr; converting enzyme (TACE), aggrecanase, or a combination thereof.

  本申请描述了具有以下式(I)的新型咪唑啉衍生物：1或其药用可接受的盐或前药形式，其中A、B、R1、R2、R3、R4、R5、R6、R7、R11和n在本说明书中有定义，这些衍生物可用作基质金属蛋白酶（MMP）、TNF-α转化酶（TACE）、聚集素酶的抑制剂，或其组合。
• Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE)
  申请人：——

  公开号：US20040067996A1

  公开（公告）日：2004-04-08

  The present application describes novel hydantoin derivatives of formula (I): 1 or pharmaceutically acceptable salt or prodrug forms thereof, wherein L, Z 0 , R 1 , R 4 , R 5 , and R 11 are defined in the present specification, which are useful as inhibitors of matrix metalloproteinases (MMP), TNF-&agr; converting enzyme (TACE), aggrecanase, or a combination thereof.

  本申请描述了式（I）的新颖咪唑烷二酮衍生物：1或其药用盐或前药形式，其中L、Z0、R1、R4、R5和R11如本规范中定义，这些衍生物可作为基质金属蛋白酶（MMP）、TNF-α转化酶（TACE）、聚集素酶的抑制剂，或者两者的组合。
• Uracil derivatives as inhibitors of TNF-alpha converting enzyme (TACE) and matrix metalloproteinases
  申请人：——

  公开号：US20030229081A1

  公开（公告）日：2003-12-11

  The present application describes novel uracil derivatives of formula I: A-W-U-X-Y-Z-U a -X a -Y a -Z a I or pharmaceutically acceptable salt or prodrug forms thereof, wherein A, W, U, X, Y, Z, U a , X a , Y a , and Z a are defined in the present specification, which are useful as inhibitors of TNF-&agr; converting enzyme (TACE), matrix metalloproteinases (MMP), aggrecanase or a combination thereof.

  本申请描述了式I的新颖尿嘧啶衍生物：A-W-U-X-Y-Z-Ua-Xa-Ya-Za或其药用可接受的盐或前药形式，其中A、W、U、X、Y、Z、Ua、Xa、Ya和Za在本规范中有定义，这些衍生物可用作肿瘤坏死因子α转化酶（TACE）、基质金属蛋白酶（MMP）、聚集素酶的抑制剂或其组合。