N-(4-chlorophenyl)-4-formyl-7-methoxy-1-benzofuran-2-carboxamide | 207561-50-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-chlorophenyl)-4-formyl-7-methoxy-1-benzofuran-2-carboxamide
• CAS: 207561-50-0
• 化学式: C₁₇H₁₂ClNO₄
• 分子量: 329.74
• InChiKey: XIPDEBITXGTBBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 N-(4-chlorophenyl)-4-formyl-7-methoxy-1-benzofuran-2-carboxamide 在 碘 、 potassium hydroxide 作用下， 生成 Methyl 2-[(4-chlorophenyl)carbamoyl]-7-methoxy-1-benzofuran-4-carboxylate
  参考文献：
  名称：

  Synthetic studies on selective adenosine A2A receptor antagonists: Synthesis and structure–activity relationships of novel benzofuran derivatives

  摘要：

  A series of benzofuran derivatives were prepared to study their antagonistic activities to the A(2A) receptor. Replacement of the ester group of the lead compound 1 with phenyl ring improved the PK profile, while modi. cations of the amide moiety showed enhanced antagonistic activity. From these studies, compounds 13c, 13f, and 24a showed good potency in vitro and were identified as novel A(2A) receptor antagonists suitable for oral activity evaluation in animal models of catalepsy. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.028
• 作为产物：
  描述：

  4-formyl-7-methoxy-benzofuran-2-carboxylic acid 、 对氯苯胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(4-chlorophenyl)-4-formyl-7-methoxy-1-benzofuran-2-carboxamide
  参考文献：
  名称：

  Synthetic studies on selective adenosine A2A receptor antagonists: Synthesis and structure–activity relationships of novel benzofuran derivatives

  摘要：

  A series of benzofuran derivatives were prepared to study their antagonistic activities to the A(2A) receptor. Replacement of the ester group of the lead compound 1 with phenyl ring improved the PK profile, while modi. cations of the amide moiety showed enhanced antagonistic activity. From these studies, compounds 13c, 13f, and 24a showed good potency in vitro and were identified as novel A(2A) receptor antagonists suitable for oral activity evaluation in animal models of catalepsy. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.028

文献信息

• DERIVATIVES OF BENZOFURAN OR BENZODIOXOLE
  申请人：——

  公开号：US20020128290A1

  公开（公告）日：2002-09-12

  An oxygen-containing heterocyclic compound represented by following Formula (I): 1 wherein R 1 and R 2 independently represent hydrogen, lower alkyl, cyano, —(CH 2 ) n —E 1 —CO—G 1 (wherein E 1 represents a bond, O, or NH; and G 1 represents hydrogen, substituted or unsubstituted lower alkyl, OR 6 , or NR 7 R 8 ; and n represents an integer of 0 to 4), or the like; R 1 and R 2 are combined to represent a saturated carbon ring together with a carbon atom adjacent thereto; or R 2 , and R 11 or R 13 described below are combined to form a single bond; R 3 represents hydrogen, phenyl, or halogen; R 4 represents hydroxy, lower alkoxy, or the like; A represents —C(R 9 )(R 10 )— or O; B represents O, NR 11 , —C(R 12 )(R 13 )—, or —C(R 14 )(R 15 )—C(R 16 )(R 17 )—; D represents (i) —C(R 18 )(R 19 )—X— (wherein X represents —C(R 21 )(R 22 )—, S, or NR 23 ), (ii) —C(R 19a )═Y— [Y represents —C(R 24 )—Z— (wherein Z represents CONH, CONHCH 2 , or a bond), or N], or (iii) a bond; and R 5 represents aryl, an aromatic heterocyclic group, cycloalkyl, pyridine-N-oxide, cyano, or lower alkoxycarbonyl; or pharmaceutically acceptable salts thereof.

  以下是由下式（I）表示的含氧杂环化合物： 其中R1和R2独立地表示氢、较低的烷基、氰基、—（CH2）n—E1—CO—G1（其中E1表示键、O或NH；G1表示氢、取代或未取代的较低烷基、OR6或NR7R8；n表示0到4的整数），或类似物；R1和R2结合表示与相邻碳原子一起形成饱和碳环；或R2，以及下文描述的R11或R13结合形成单键；R3表示氢、苯基或卤素；R4表示羟基、较低的烷氧基或类似物；A表示—C（R9）（R10）—或O；B表示O、NR11、—C（R12）（R13）—或—C（R14）（R15）—C（R16）（R17）—；D表示（i）—C（R18）（R19）—X—（其中X表示—C（R21）（R22）—、S或NR23）、（ii）—C（R19a）═Y—［Y表示—C（R24）—Z—（其中Z表示CONH、CONHCH2或键），或N］，或（iii）键；R5表示芳基、芳香杂环基、环烷基、吡啶-N-氧化物、氰基或较低烷氧羰基；或其药学上可接受的盐。
• US6514996B2
  申请人：——

  公开号：US6514996B2

  公开（公告）日：2003-02-04
• US6716987B1
  申请人：——

  公开号：US6716987B1

  公开（公告）日：2004-04-06
• Synthetic studies on selective adenosine A2A receptor antagonists: Synthesis and structure–activity relationships of novel benzofuran derivatives
  作者：Osamu Saku、Mayumi Saki、Masako Kurokawa、Ken Ikeda、Takuya Takizawa、Noriaki Uesaka

  DOI：10.1016/j.bmcl.2009.12.028

  日期：2010.2

  A series of benzofuran derivatives were prepared to study their antagonistic activities to the A(2A) receptor. Replacement of the ester group of the lead compound 1 with phenyl ring improved the PK profile, while modi. cations of the amide moiety showed enhanced antagonistic activity. From these studies, compounds 13c, 13f, and 24a showed good potency in vitro and were identified as novel A(2A) receptor antagonists suitable for oral activity evaluation in animal models of catalepsy. (C) 2009 Elsevier Ltd. All rights reserved.