tert-butyl N-[(1S,2R)-2-hydroxy-1-(phenylsulfanylmethyl)propyl]carbamate | 129396-94-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: tert-butyl N-[(1S,2R)-2-hydroxy-1-(phenylsulfanylmethyl)propyl]carbamate
• 英文别名: tert-butyl N-[(2S,3R)-3-hydroxy-1-phenylsulfanylbutan-2-yl]carbamate
• CAS: 129396-94-7
• 化学式: C₁₅H₂₃NO₃S
• 分子量: 297.419
• InChiKey: IODRNZJREJNDGJ-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S,2R)-2-hydroxy-1-(phenylsulfanylmethyl)propyl]carbamate 在 盐酸 、 三乙胺 作用下， 以 甲醇 、 水 、 正丁醇 为溶剂， 反应 3.0h， 生成 (2R,3S)-3-(6-chloropurin-9-yl)-4-phenylsulfanylbutan-2-ol
  参考文献：
  名称：

  Modifications of flexible nonyl chain and nucleobase head group of (+)-erythro-9-(2′s-hydroxy-3′s-nonyl)adenine [(+)-EHNA] as adenosine deaminase inhibitors

  摘要：

  A series of terminal nonyl chain and nucleobase modified analogues of (+)-EHNA (III) were synthesized and evaluated for their ability to inhibit adenosine deaminase (ADA). The constrained carbon analogues of (+)-EHNA, 7a-7h, 10a-c, 12, 13, 14 and 17a-c appeared very potent with Ki values in the low nanomolar range. Thio-analogues of (+)-EHNA 24a-e wherein 5 ' C of nonyl chain replaced by sulfur atom found to be less potent compared to (+)-EHNA. Docking of the representative compounds into the active site of ADA was performed to understand structure-activity relationships. Compounds 7a (Ki: 1.1 nM) 7b (Ki: 5.2 nM) and 26a (Ki: 5.9 nM) showed suitable balance of potency, microsomal stability and demonstrated better pharmacokinetic properties as compared to (+)-EHNA and therefore may have therapeutic potential for various inflammatory diseases, hypertension and cancer. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.09.015
• 作为产物：
  描述：

  BOC-苏氨酸甲酯 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 tert-butyl N-[(1S,2R)-2-hydroxy-1-(phenylsulfanylmethyl)propyl]carbamate
  参考文献：
  名称：

  Modifications of flexible nonyl chain and nucleobase head group of (+)-erythro-9-(2′s-hydroxy-3′s-nonyl)adenine [(+)-EHNA] as adenosine deaminase inhibitors

  摘要：

  A series of terminal nonyl chain and nucleobase modified analogues of (+)-EHNA (III) were synthesized and evaluated for their ability to inhibit adenosine deaminase (ADA). The constrained carbon analogues of (+)-EHNA, 7a-7h, 10a-c, 12, 13, 14 and 17a-c appeared very potent with Ki values in the low nanomolar range. Thio-analogues of (+)-EHNA 24a-e wherein 5 ' C of nonyl chain replaced by sulfur atom found to be less potent compared to (+)-EHNA. Docking of the representative compounds into the active site of ADA was performed to understand structure-activity relationships. Compounds 7a (Ki: 1.1 nM) 7b (Ki: 5.2 nM) and 26a (Ki: 5.9 nM) showed suitable balance of potency, microsomal stability and demonstrated better pharmacokinetic properties as compared to (+)-EHNA and therefore may have therapeutic potential for various inflammatory diseases, hypertension and cancer. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.09.015

文献信息

• A New Synthetic Approach to (+)-Galantinic Acid, Degradation Product from the Peptide Antibiotic Galantin I, via 4-Amino-3-hydroxypyranose
  作者：Shinzo Kano、Tsutomu Yokomatsu、Shiroshi Shibuya

  DOI：10.3987/com-89-5207

  日期：——
• KANO, SHINZO;YOKOMATSU, TSUTOMU;SHIBUYA, SHIROSHI, HETEROCYCLES, 31,(1990) N, C. 13-16
  作者：KANO, SHINZO、YOKOMATSU, TSUTOMU、SHIBUYA, SHIROSHI

  DOI：——

  日期：——