((2S,3R)-3-hydroxy-4-(N-isobutylbenzo[d]thiazole-6-sulfonamido)-1-phenylbutan-2-yl)carbamic acid tert-butyl ester | 183004-96-8

• 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: ((2S,3R)-3-hydroxy-4-(N-isobutylbenzo[d]thiazole-6-sulfonamido)-1-phenylbutan-2-yl)carbamic acid tert-butyl ester
• 英文别名: N-[(1S,2R)-3-[(6-benzothiazolylsulfonyl)-(2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-carbamic acid-1,1-dimethylethyl ester；2R-hydroxy-3-[(benzothiazole-6-sulfonyl) (2-methylpropyl)amino]-1S-(phenylmethyl) propylcarbamic acid t-butyl ester；2R-hydroxy-3-[[(benzothiazol-6-yl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propylcarbamic acid t-butyl ester；›2R-hydroxy-3-[[(benzothiazol-6-yl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl) propylcarbamic acid t-butyl ester；›2R-hydroxy-3-[(benzothiazole-6-sulfonyl)(2-methylpropyl)amino]-1S-(phenylmethyl)propylcarbamic acid t-butyl ester；tert-butyl N-[(2S,3R)-4-[1,3-benzothiazol-6-ylsulfonyl(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
• CAS: 183004-96-8
• 化学式: C₂₆H₃₅N₃O₅S₂
• 分子量: 533.713
• InChiKey: WAPNAYCXTXZQIZ-XZOQPEGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  145
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ((2S,3R)-3-hydroxy-4-(N-isobutylbenzo[d]thiazole-6-sulfonamido)-1-phenylbutan-2-yl)carbamic acid tert-butyl ester 在 盐酸 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (R)-N-{(1S,2R)-3-[(Benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-3-methanesulfonyl-2-methyl-propionamide
  参考文献：
  名称：

  Discovery of novel benzothiazolesulfonamides as potent inhibitors of HIV-1 protease

  摘要：

  The human immunodeficiency virus (HIV) has been shown to be the causative agent for AIDS. The HIV virus encodes for a unique aspartyl protease that is essential for the production of enzymes and proteins in the final stages of maturation. Protease inhibitors have been useful in combating the disease. The inhibitors incorporate a variety of isosteres including the hydroxy-ethylurea at the protease cleavage site. We have shown that the replacement of t-butylurea moiety by benzothiazolesulfonamide provided inhibitors with improved potency and antiviral activities. Some of the compounds have shown good oral bioavailability and half-life in rats. The synthesis of benzothiazole derivatives led us to explore other heterocycles. During the course of our Studies. we also developed an efficient synthesis of benzothiazole-6-sulfonic acid via a two-step procedure starting from sulfanilamide. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.07.001
• 作为产物：
  描述：

  [(1S,2R)-1-苄基-1-苄氧羰基氨基-2-羟基-4-N-异丁基氨基丙烷 在 palladium on activated charcoal 氢气 、 copper(II) sulfate 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 36.0h， 生成 ((2S,3R)-3-hydroxy-4-(N-isobutylbenzo[d]thiazole-6-sulfonamido)-1-phenylbutan-2-yl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  Discovery of novel benzothiazolesulfonamides as potent inhibitors of HIV-1 protease

  摘要：

  The human immunodeficiency virus (HIV) has been shown to be the causative agent for AIDS. The HIV virus encodes for a unique aspartyl protease that is essential for the production of enzymes and proteins in the final stages of maturation. Protease inhibitors have been useful in combating the disease. The inhibitors incorporate a variety of isosteres including the hydroxy-ethylurea at the protease cleavage site. We have shown that the replacement of t-butylurea moiety by benzothiazolesulfonamide provided inhibitors with improved potency and antiviral activities. Some of the compounds have shown good oral bioavailability and half-life in rats. The synthesis of benzothiazole derivatives led us to explore other heterocycles. During the course of our Studies. we also developed an efficient synthesis of benzothiazole-6-sulfonic acid via a two-step procedure starting from sulfanilamide. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.07.001

文献信息

• Sulfonylalkanoylamino hydroxyethylamino sulfonamide retroviral protease
  申请人：G.D. Searle & Co.

  公开号：US05985870A1

  公开（公告）日：1999-11-16

  Selected sulfonylalkanoylamino hydroxyethylamine sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to such retroviral protease inhibitors and, more particularly, relates to selected novel compounds, composition and method for inhibiting retroviral proteases, such as human immunodeficiency virus (HIV) protease, prophylactically preventing retroviral infection or the spread of a retrovirus, and treatment of a retroviral infection.

  选定的磺胺烷酰胺羟乙基胺磺酰胺化合物作为逆转录病毒蛋白酶抑制剂具有有效性，特别是作为HIV蛋白酶的抑制剂。本发明涉及这种逆转录病毒蛋白酶抑制剂，更特别地涉及选定的新化合物、组合物和用于抑制逆转录病毒蛋白酶的方法，例如人类免疫缺陷病毒（HIV）蛋白酶，预防逆转录病毒感染或逆转录病毒的传播，以及治疗逆转录病毒感染。
• Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
  申请人：G. D. Searle & Co.

  公开号：US06388132B1

  公开（公告）日：2002-05-14

  Selected bis-amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to such retroviral protease inhibitors and, more particularly, relates to selected novel compounds, composition and method for inhibiting retroviral proteases, such as human immunodeficiency virus (HIV) protease, prophylactically preventing retroviral infection or the spread of a retrovirus, and treatment of a retroviral infection.

  选定的双氨基酸羟乙基氨基磺胺化合物作为逆转录病毒蛋白酶抑制剂具有良好的效果，特别是作为HIV蛋白酶的抑制剂。本发明涉及这类逆转录病毒蛋白酶抑制剂，更具体地涉及选定的新化合物、组合物和方法，用于抑制逆转录病毒蛋白酶，如人类免疫缺陷病毒（HIV）蛋白酶，预防逆转录病毒感染或传播，以及治疗逆转录病毒感染。
• Amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
  申请人：G. D. Searle & Company

  公开号：US05968970A1

  公开（公告）日：1999-10-19

  Described herein is a retroviral protease inhibiting compound of the formula: ##STR1## or a pharmaceutically acceptable salt, prodrug or ester thereof.

  本文描述了一种抑制逆转录病毒蛋白酶的化合物，其化学式为：##STR1## 或其药用可接受的盐、前药或酯。
• Bis-amino acid hydroxyethlamino sulfonamide retroviral protease
  申请人：G.D. Searle & Co.

  公开号：US06143788A1

  公开（公告）日：2000-11-07

  Selected bis-amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to such retroviral protease inhibitors and, more particularly, relates to selected novel compounds, composition and method for inhibiting retroviral proteases, such as human immunodeficiency virus (HIV) protease, prophylactically preventing retroviral infection or the spread of a retrovirus, and treatment of a retroviral infection.

  选定的双氨基酸羟乙基氨基磺酰胺化合物作为逆转录病毒蛋白酶抑制剂具有良好效果，特别是作为HIV蛋白酶的抑制剂。本发明涉及这种逆转录病毒蛋白酶抑制剂，更具体地涉及选定的新化合物、组合物和方法，用于抑制逆转录病毒蛋白酶，如人类免疫缺陷病毒（HIV）蛋白酶，预防逆转录病毒感染或逆转录病毒的传播，并治疗逆转录病毒感染。
• Bis-amino acid hydroxyethylamino sulfonamide retroviral protease
  申请人：G. D. Dearle & Co.

  公开号：US06150556A1

  公开（公告）日：2000-11-21

  Selected bis-amino acid hydroxyethylamino sulfonamide compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to such retroviral protease inhibitors and, more particularly, relates to selected novel compounds, composition and method for inhibiting retroviral proteases, such as human immunodeficiency virus (HIV) protease, prophylactically preventing retroviral infection or the spread of a retrovirus, and treatment of a retroviral infection.

  选定的双氨基酸羟乙基氨基磺酰胺化合物作为逆转录病毒蛋白酶抑制剂具有良好的效果，特别是作为HIV蛋白酶的抑制剂。本发明涉及这种逆转录病毒蛋白酶抑制剂，更具体地涉及选定的新化合物、组合物和方法，用于抑制逆转录病毒蛋白酶，如人类免疫缺陷病毒（HIV）蛋白酶，预防逆转录病毒感染或传播，以及治疗逆转录病毒感染。