4-(3-bromo-propoxy)-3-methyl-benzofuran-2-carboxylic acid | 279230-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 4-(3-bromo-propoxy)-3-methyl-benzofuran-2-carboxylic acid
• 英文别名: 4-(3-bromopropoxy)-3-methyl-1-benzofuran-2-carboxylic acid
• CAS: 279230-92-1
• 化学式: C₁₃H₁₃BrO₄
• 分子量: 313.148
• InChiKey: WGPHSHOZFWKBAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3-bromo-propoxy)-3-methyl-benzofuran-2-carboxylic acid 在 氯化亚砜 、 TEA 作用下， 以 氯仿 为溶剂， 生成 4-(3-Bromo-propoxy)-3-methyl-benzofuran-2-carboxylic acid phenylamide
  参考文献：
  名称：

  Design and synthesis of novel benzofurans as a new class of antifungal agents targeting fungal N-myristoyltransferase. Part 2

  摘要：

  Modification of the C-2 position of a benzofuran derivative 6 (RO-09-4609), an N-myristoyltransferase (Nmt) inhibitor, has led us to discover antifungal agents that are active in a murine systemic candidiasis model. The drug design is based on the analysis of a crystal structure of a Candida Nmt complex with 2. The optimization has been guided by various biological evaluations including a quasi in vivo assay and pharmacokinetic analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00808-3
• 作为产物：
  描述：

  4-(3-bromopropoxy)-3-methylbenzofuran-2-carboxylic acid ethyl ester 在 氢氧化钾 作用下， 生成 4-(3-bromo-propoxy)-3-methyl-benzofuran-2-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of novel benzofurans as a new class of antifungal agents targeting fungal N-myristoyltransferase. Part 3

  摘要：

  A new series of acid-stable antifungal agents having strong inhibitory activity against Candida albicans N-myristoyl-transferase (CaNmt) has been developed starting from acid-unstable benzofuranylmethyl aryl ether 2. The inhibitor design is based on X-ray crystallographic analysis of a CaNmt complex with aryl ether 3. Among the new inhibitors, pyridine derivative 8b and benzimidazole derivative 8k showed clear antifungal activity in a murine systemic candidiasis model. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00844-2

文献信息

• Bicyclic compounds
  申请人：Basilea Pharmaceutica AG

  公开号：US06376491B1

  公开（公告）日：2002-04-23

  The present invention is directed to new bicyclic compounds of the formula [I], and pharmaceutically acceptable salts thereof wherein R1, R2, R3, R4, R5, R6, R7, Q1 Q2 and Q3 are as defined in the claims. The compounds have N-myristoyltransferase inhibitory and antifungal activity.

  本发明涉及公式［I］的新的双环化合物及其药学上可接受的盐，其中R1、R2、R3、R4、R5、R6、R7、Q1、Q2和Q3如权利要求中所定义。这些化合物具有N-肉豆蔻酰基转移酶抑制和抗真菌活性。
• 4-(AMINOALKOXY)BENZOFURANS AS N-MYRISTOYLTRANSFERASE INHIBITORS
  申请人：Basilea Pharmaceutica AG

  公开号：EP1149094B1

  公开（公告）日：2004-04-21
• US6376491B1
  申请人：——

  公开号：US6376491B1

  公开（公告）日：2002-04-23
• [EN] NOVEL BICYCLIC COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES BICYCLIQUES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2000037464A2

  公开（公告）日：2000-06-29

  The present invention is directed to new bicyclic compounds of formula (I), and pharmaceutically acceptable salts thereof wherein R?1, R2, R3, R4, R5, R6, R7, Q1 Q2 and Q3¿ are as defined in the claims. The compounds have N-myristoyltransferase inhibitory and antifungal activity.
• Design and synthesis of novel benzofurans as a new class of antifungal agents targeting fungal N-myristoyltransferase. Part 2
  作者：Hirosato Ebiike、Miyako Masubuchi、Pingli Liu、Ken-ichi Kawasaki、Kenji Morikami、Satoshi Sogabe、Michiko Hayase、Toshihiko Fujii、Kiyoaki Sakata、Hidetoshi Shindoh、Yasuhiko Shiratori、Yuko Aoki、Tatsuo Ohtsuka、Nobuo Shimma

  DOI：10.1016/s0960-894x(01)00808-3

  日期：2002.2

  Modification of the C-2 position of a benzofuran derivative 6 (RO-09-4609), an N-myristoyltransferase (Nmt) inhibitor, has led us to discover antifungal agents that are active in a murine systemic candidiasis model. The drug design is based on the analysis of a crystal structure of a Candida Nmt complex with 2. The optimization has been guided by various biological evaluations including a quasi in vivo assay and pharmacokinetic analysis. (C) 2002 Elsevier Science Ltd. All rights reserved.