4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-3-methyl-isoxazolo[5,4-b]pyridine-5-carboxylic acid ethyl ester | 287379-35-5

• 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: 4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-3-methyl-isoxazolo[5,4-b]pyridine-5-carboxylic acid ethyl ester
• 英文别名: ethyl 4-[(4-but-2-ynoxyphenyl)sulfonyl-methylamino]-3-methyl-[1,2]oxazolo[5,4-b]pyridine-5-carboxylate
• CAS: 287379-35-5
• 化学式: C₂₁H₂₁N₃O₆S
• 分子量: 443.48
• InChiKey: LWUJGISRZFNSOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-3-methyl-isoxazolo[5,4-b]pyridine-5-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 生成 4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-3-methyl-isoxazolo[5,4-b]pyridine-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and SAR of bicyclic heteroaryl hydroxamic acid MMP and TACE inhibitors

  摘要：

  Potent and selective bicyclic heteroaryl hydroxamic acid MMP and TACE inhibitors were synthesized by a novel convergent route. Selectivity and efficacy versus MMPs and TACE could be controlled by appropriate substitution on the scaffolds and by variation of the P1' group. Select compounds were found to be effective in in vivo models of arthritis. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00127-6
• 作为产物：
  描述：

  3-methyl-4-oxo-4,7-dihydro-isoxazolo[5,4-b]pyridine-5-carboxylic acid ethyl ester 在 sodium hydride 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-[(4-but-2-ynyloxy-benzenesulfonyl)-methyl-amino]-3-methyl-isoxazolo[5,4-b]pyridine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and SAR of bicyclic heteroaryl hydroxamic acid MMP and TACE inhibitors

  摘要：

  Potent and selective bicyclic heteroaryl hydroxamic acid MMP and TACE inhibitors were synthesized by a novel convergent route. Selectivity and efficacy versus MMPs and TACE could be controlled by appropriate substitution on the scaffolds and by variation of the P1' group. Select compounds were found to be effective in in vivo models of arthritis. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00127-6

文献信息

• Preparation and use of acetylenic ortho-sulfonamido and phosphinic acid amido bicyclic heteroaryl hydroxamic acids as TACE inhibitors
  申请人：American Cyanamid Company

  公开号：US20030208066A1

  公开（公告）日：2003-11-06

  Compounds of the formula 1 which are useful in disease conditions mediated by TNF-&agr;, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.

  式1的化合物在由TNF-α介导的疾病条件中很有用，如类风湿关节炎、骨关节炎、败血症、艾滋病、溃疡性结肠炎、多发性硬化症、克罗恩病和软骨退行性损失。
• ACETYLENIC ORTHO-SULFONAMIDO AND PHOSPHINIC ACID AMIDO BICYCLIC HETEROARYL HYDROXAMIC ACIDS AS TACE INHIBITORS
  申请人：American Cyanamid Company

  公开号：EP1157024B1

  公开（公告）日：2002-11-06
• US6946473B2
  申请人：——

  公开号：US6946473B2

  公开（公告）日：2005-09-20
• [EN] ACETYLENIC ORTHO-SULFONAMIDO AND PHOSPHINIC ACID AMIDO BICYCLIC HETEROARYL HYDROXAMIC ACIDS AS TACE INHIBITORS<br/>[FR] ACIDES HYDROXAMIQUES ACETHYLENIQUE-ORTHO-SULFAMIDO ET PHOSPHINIQUE-AMIDO BICYCLIQUE HETEROARYLE UTILISES EN TANT QU'INHIBITEURS DE L'ENZYME DE CONVERSION DU TNF- DOLLAR G(A) OU "TACE"
  申请人：AMERICAN CYANAMID CO

  公开号：WO2000044749A1

  公开（公告）日：2000-08-03

  Compounds of formulas (a), (b), (c), or (d) are provided wherein P and Q are (e) or (f), provided that when P is (e), Q is (f), and vice versa; which are useful in disease conditions mediated by TNF-α, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.
• Synthesis and SAR of bicyclic heteroaryl hydroxamic acid MMP and TACE inhibitors
  作者：A. Zask、Y. Gu、J.D. Albright、X. Du、M. Hogan、J.I. Levin、J.M. Chen、L.M. Killar、A. Sung、J.F. DiJoseph、M.A. Sharr、C.E. Roth、S. Skala、G. Jin、R. Cowling、K.M. Mohler、D. Barone、R. Black、C. March、J.S. Skotnicki

  DOI：10.1016/s0960-894x(03)00127-6

  日期：2003.4

  Potent and selective bicyclic heteroaryl hydroxamic acid MMP and TACE inhibitors were synthesized by a novel convergent route. Selectivity and efficacy versus MMPs and TACE could be controlled by appropriate substitution on the scaffolds and by variation of the P1' group. Select compounds were found to be effective in in vivo models of arthritis. (C) 2003 Elsevier Science Ltd. All rights reserved.