{3-[2-(4,5-dimethyl-thiazole-2-carbonyl)-3-methyl-benzofuran-4-yloxy]-propyl}-pyridin-3-ylmethyl-carbamic acid tert-butyl ester | 279231-50-4

• 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: {3-[2-(4,5-dimethyl-thiazole-2-carbonyl)-3-methyl-benzofuran-4-yloxy]-propyl}-pyridin-3-ylmethyl-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[3-[[2-(4,5-dimethyl-1,3-thiazole-2-carbonyl)-3-methyl-1-benzofuran-4-yl]oxy]propyl]-N-(pyridin-3-ylmethyl)carbamate
• CAS: 279231-50-4
• 化学式: C₂₉H₃₃N₃O₅S
• 分子量: 535.664
• InChiKey: NSSODAUPIYIADS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  {3-[2-(4,5-dimethyl-thiazole-2-carbonyl)-3-methyl-benzofuran-4-yloxy]-propyl}-pyridin-3-ylmethyl-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (4,5-dimethyl-thiazol-2-yl)-(3-methyl-4-{3-[(pyridin-3-ylmethyl)-amino]-propoxy}-benzofuran-2-yl)-methanone
  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
• 作为产物：
  描述：

  4-(3-bromopropoxy)-3-methylbenzofuran-2-carboxylic acid ethyl ester 在 氢氧化钾 、 草酰氯 作用下， 以 乙醇 为溶剂， 生成 {3-[2-(4,5-dimethyl-thiazole-2-carbonyl)-3-methyl-benzofuran-4-yloxy]-propyl}-pyridin-3-ylmethyl-carbamic acid tert-butyl ester
  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
• Design and synthesis of novel benzofurans as a new class of antifungal agents targeting fungal N-myristoyltransferase. Part 3
  作者：Ken-ichi Kawasaki、Miyako Masubuchi、Kenji Morikami、Satoshi Sogabe、Tsunehisa Aoyama、Hirosato Ebiike、Satoshi Niizuma、Michiko Hayase、Toshihiko Fujii、Kiyoaki Sakata、Hidetoshi Shindoh、Yasuhiko Shiratori、Yuko Aoki、Tatsuo Ohtsuka、Nobuo Shimma

  DOI：10.1016/s0960-894x(02)00844-2

  日期：2003.1

  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.