2R-hydroxy-3-[(3-aminophenylsulfonyl) (2-methylpropyl) amino]-1S-(phenylmethyl)propylcarbamic acid phenylmethyl ester | 181124-54-9

• 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: 2R-hydroxy-3-[(3-aminophenylsulfonyl) (2-methylpropyl) amino]-1S-(phenylmethyl)propylcarbamic acid phenylmethyl ester
• 英文别名: carbamic acid, 2R-hydroxy-3-[[(3-aminophenyl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propyl-, phenylmethyl ester；benzyl N-[(2S,3R)-4-[(3-aminophenyl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
• CAS: 181124-54-9
• 化学式: C₂₈H₃₅N₃O₅S
• 分子量: 525.669
• InChiKey: DIFVCROYWMZDLW-RRPNLBNLSA-N

物化性质

• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  potassium thioacyanate 、 2R-hydroxy-3-[(3-aminophenylsulfonyl) (2-methylpropyl) amino]-1S-(phenylmethyl)propylcarbamic acid phenylmethyl ester 在 copper(II) sulfate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以45%的产率得到carbamic acid, 2R-hydroxy-3-[[(2-aminobenzothiazol-7-yl)sulfonyl](2-methylpropyl)amino]-1S-(phenylmethyl)propyl-, phenylmethyl ester
  参考文献：
  名称：

  Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors

  摘要：

  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。

  公开号：

  US06388132B1
• 作为产物：
  描述：

  3-硝基苯磺酰氯 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 2R-hydroxy-3-[(3-aminophenylsulfonyl) (2-methylpropyl) amino]-1S-(phenylmethyl)propylcarbamic acid phenylmethyl 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

• 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。
• Bis-sulfonamide hydroxyethylamino retroviral protease inhibitors
  申请人：Freskos N. John

  公开号：US20060199822A1

  公开（公告）日：2006-09-07

  Bis-sulfonamido hydroxyethylamino compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to retroviral protease inhibiting compounds of the formula: or a pharmaceutically acceptable salt, prodrug or ester thereof, wherein the variables are as defined herein.

  双磺酰胺羟乙基氨化合物作为逆转录病毒蛋白酶抑制剂具有良好的效果，尤其是对HIV蛋白酶的抑制作用。本发明涉及公式所示的逆转录病毒蛋白酶抑制化合物：或其药学上可接受的盐、前药或酯，其中变量的定义如本文所述。
• BIS-SULFONAMIDE HYDROXYETHYLAMINO RETROVIRAL PROTEASE INHIBITORS
  申请人：Freskos John N.

  公开号：US20080176842A1

  公开（公告）日：2008-07-24

  Bis-sulfonamido hydroxyethylamino compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease. The present invention relates to retroviral protease inhibiting compounds of the formula: or a pharmaceutically acceptable salt, prodrug or ester thereof, wherein the variables are as defined herein.

  双磺酰胺羟乙基氨基化合物在抗逆转录病毒蛋白酶中具有有效性，特别是在抑制HIV蛋白酶方面具有作用。本发明涉及以下式子的抗逆转录病毒蛋白酶抑制化合物：或其药学上可接受的盐、前药或酯，其中变量如本文所定义。
• US6384036B1
  申请人：——

  公开号：US6384036B1

  公开（公告）日：2002-05-07
• US7297793B2
  申请人：——

  公开号：US7297793B2

  公开（公告）日：2007-11-20