4-(chloromethyl)-4-hydroxy-2-isopropyloxazoline | 162739-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 4-(chloromethyl)-4-hydroxy-2-isopropyloxazoline
• 英文别名: 4-Chloromethyl-4-hydroxy-2-isopropyloxazoline；4-Chloromethyl-4-hydroxy-2-isopropyoxazoline；4-(chloromethyl)-2-propan-2-yl-5H-1,3-oxazol-4-ol
• CAS: 162739-93-7
• 化学式: C₇H₁₂ClNO₂
• 分子量: 177.631
• InChiKey: MMYDHLZIVNPYOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(chloromethyl)-4-hydroxy-2-isopropyloxazoline 在 氯化亚砜 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 1.25h， 生成 2-isopropyl-4-<(N-methylamino)methyl>oxazole
  参考文献：
  名称：

  Discovery of Ritonavir, a Potent Inhibitor of HIV Protease with High Oral Bioavailability and Clinical Efficacy

  摘要：

  The structure-activity studies leading to the potent and clinically efficacious HIV protease inhibitor ritonavir are described. Beginning with the moderately potent and orally bioavailable inhibitor A-80987, systematic investigation of peripheral (P3 and P2') heterocyclic groups designed to decrease the rate of hepatic metabolism provided analogues with improved pharmacokinetic properties after oral dosing in rats. Replacement of pyridyl groups with thiazoles provided increased chemical stability toward oxidation while maintaining sufficient aqueous solubility for oral absorption, Optimization of hydrophobic interactions with the HIV protease active site produced ritonavir, with excellent in vitro potency (EC50 = 0.02 mu M) and high and sustained plasma concentrations after oral administration in four species. Details of the discovery and preclinical development of ritonavir are described.

  DOI：

  10.1021/jm970636+
• 作为产物：
  描述：

  异丁酰胺 、 1,3-二氯丙酮 在 碳酸氢钠 、 magnesium sulfate 作用下， 以 丙酮 为溶剂， 反应 63.0h， 以46%的产率得到4-(chloromethyl)-4-hydroxy-2-isopropyloxazoline
  参考文献：
  名称：

  Discovery of Ritonavir, a Potent Inhibitor of HIV Protease with High Oral Bioavailability and Clinical Efficacy

  摘要：

  The structure-activity studies leading to the potent and clinically efficacious HIV protease inhibitor ritonavir are described. Beginning with the moderately potent and orally bioavailable inhibitor A-80987, systematic investigation of peripheral (P3 and P2') heterocyclic groups designed to decrease the rate of hepatic metabolism provided analogues with improved pharmacokinetic properties after oral dosing in rats. Replacement of pyridyl groups with thiazoles provided increased chemical stability toward oxidation while maintaining sufficient aqueous solubility for oral absorption, Optimization of hydrophobic interactions with the HIV protease active site produced ritonavir, with excellent in vitro potency (EC50 = 0.02 mu M) and high and sustained plasma concentrations after oral administration in four species. Details of the discovery and preclinical development of ritonavir are described.

  DOI：

  10.1021/jm970636+

文献信息

• Retroviral protease inhibiting piperazine compounds
  申请人：Abbott Laboratories

  公开号：US05455351A1

  公开（公告）日：1995-10-03

  Retroviral protease inhibiting compounds of the formula: ##STR1## are disclosed.

  翻译结果为：公开了具有以下公式的逆转录病毒蛋白酶抑制化合物：##STR1##。
• Retroviral protease inhibiting compounds
  申请人：Abbott Laboratories

  公开号：US05461067A1

  公开（公告）日：1995-10-24

  A retroviral protease inhibiting compound of the formula: ##STR1## is disclosed wherein R.sub.1, R.sub.2, R.sub.5, R.sub.6, Y.sub.m and Y'.sub.n are herein defined.

  公开了一种化学式为##STR1##的逆转录病毒蛋白酶抑制化合物，其中R.sub.1、R.sub.2、R.sub.5、R.sub.6、Y.sub.m和Y'.sub.n在此有定义。
• [EN] RETROVIRAL PROTEASE INHIBITING COMPOUNDS<br/>[FR] COMPOSES INHIBANT DES PROTEASES RETROVIRALES
  申请人：ABBOTT LABORATORIES

  公开号：WO1994014436A1

  公开（公告）日：1994-07-07

  (EN) A retroviral protease inhibiting compound of formula (A) is disclosed.(FR) L'invention se rapporte à un composé inhibant des protéases rétrovirales, qui est présenté par la formule (A).

  一种抑制反转录病毒蛋白酶的化合物公式（A）已被披露。(法语)本发明涉及一种通过公式（A）表示的抑制反转录病毒蛋白酶的化合物。
• Intermediate for making retroviral protease inhibiting compounds
  申请人：Abbott Laboratories

  公开号：US05696270A1

  公开（公告）日：1997-12-09

  A retroviral protease inhibiting compound of the formula: ##STR1## is disclosed.

  公开一种化合物，其化学式为##STR1##，可抑制反转录病毒蛋白酶。
• Process for making retroviral protease inhibiting compounds
  申请人：Abbott Labortories

  公开号：US05892052A1

  公开（公告）日：1999-04-06

  A retroviral protease inhibiting compound of the formula: ##STR1## is disclosed.

  公开了一种化学式为##STR1##的逆转录病毒蛋白酶抑制剂。