{(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-carbamic acid tetrahydro-furan-3-yl ester | 656236-19-0

• 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: {(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-carbamic acid tetrahydro-furan-3-yl ester
• 英文别名: Tetrahydrofuran-3-yl {(1S,2R)-3-[[(2-amino-1,3-benzothiazol-6-yl)sulfonyl](isobutyl)amino]-1-benzyl-2-hydroxypropyl}carbamate；oxolan-3-yl N-[(2S,3R)-4-[(2-amino-1,3-benzothiazol-6-yl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate
• CAS: 656236-19-0
• 化学式: C₂₆H₃₄N₄O₆S₂
• 分子量: 562.711
• InChiKey: ULZZRXKZCWEBLY-NWZLQDFTSA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  181
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  {(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-carbamic acid tetrahydro-furan-3-yl ester 在 亚硝酸异戊酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以89%的产率得到{(1S,2R)-3-[(Benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid tetrahydro-furan-3-yl 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
• 作为产物：
  描述：

  3-羟基四氢呋喃 、 N,N'-二琥珀酰亚胺基碳酸酯 、 3-S-amino-2R-hydroxy-1-[(2-aminobenzothiazol-6-sulfonyl)(2-methylpropyl)amino]-4-phenylbutane 在 吡啶 作用下， 以 乙腈 为溶剂， 反应 16.5h， 以50%的产率得到{(1S,2R)-3-[(2-amino-benzothiazole-6-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxypropyl}-carbamic acid tetrahydro-furan-3-yl 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

• Discovery of novel benzothiazolesulfonamides as potent inhibitors of HIV-1 protease
  作者：Srinivasan R Nagarajan、Gary A De Crescenzo、Daniel P Getman、Hwang-Fun Lu、James A Sikorski、Jeffrey L Walker、Joseph J McDonald、Kathryn A Houseman、Geralyn P Kocan、Nandini Kishore、Pramod P Mehta、Christie L Funkes-Shippy、Lisa Blystone

  DOI：10.1016/j.bmc.2003.07.001

  日期：2003.11

  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.