(S)-1-mercaptopropan-2-ol | 120158-17-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-mercaptopropan-2-ol
• 英文别名: (2S)-1-sulfanylpropan-2-ol
• CAS: 120158-17-0
• 化学式: C₃H₈OS
• 分子量: 92.1619
• InChiKey: FETFXNFGOYOOSP-VKHMYHEASA-N

物化性质

• 沸点：
  146.0±0.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  布雷非德菌素 A 、 (S)-1-mercaptopropan-2-ol 在 1,8-双二甲氨基萘 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 2,3-dihydro-(3R)-[(2'S)-hydroxypropylthio]brefeldin A
  参考文献：
  名称：

  Preparation and Evaluation of Sulfide Derivatives of the Antibiotic Brefeldin A as Potential Prodrug Candidates with Enhanced Aqueous Solubilities

  摘要：

  Several sulfide (+)-brefeldin A (BFA) analogues were prepared through the Michael addition of various thiols. Many of the sulfides were also oxidized to the corresponding sulfoxide with m-CPBA. The sulfides were designed to act as BFA prodrugs via the metabolic oxidation to the sulfoxide and subsequent syn elimination. Kinetic experiments were used to prove that the syn elimination of the sulfoxides prepared did in fact take place. Five selenide BFA prodrugs were also prepared that are envisioned to act in the same manner as the sulfides. As expected, when oxidation of the selenide to selenoxide was attempted, in situ syn elimination was observed. All of the compounds prepared were evaluated for antiproliferative activity against human cancer cell lines in the National Cancer Institute screen. The sulfoxides were much more potent than either the sulfides or selenides. Especially notable were sulfoxide 21, which possessed a cytotoxicity mean graph midpoint value (MGM) value lower than BFA itself, and sulfoxide 22, which possessed an MGM value slightly less potent than that of BFA. The sulfide analogues were shown to possess increased aqueous solubilty with respect to BFA.

  DOI：

  10.1021/jm010054z
• 作为产物：
  描述：

  (S)-(+)-2-羟丙基对甲苯磺酸盐 在 sodium hydrogen sulfide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 (S)-1-mercaptopropan-2-ol
  参考文献：
  名称：

  [EN] TRICYCLIC PYRIDONES AND PYRIMIDONES
  [FR] PYRIDONES ET PYRIMIDONES TRICYCLIQUES

  摘要：

  公开号：

  WO2021127404A8

文献信息

• Asymmetric Reduction of α-(Dimethylthiocarbamoylthio) Carbonyl Compounds with Bakers’ Yeast
  作者：Sadao Tsuboi、Noriyuki Kohara、Katsumi Doi、Masanori Utaka、Akira Takeda

  DOI：10.1246/bcsj.61.3205

  日期：1988.9

  Treatment of α-(dimethylthiocarbamoylthio) ketones with bakers’ yeast afforded the corresponding chiral alcohols in high yields with high enantiomeric excess (in most cases, more than 96% ee). α-(Dimethylthiocarbamoylthio) aldehydes were reduced to give chiral α-(dimethylthiocarbamoylthio) alcohols in 69–92% yields with 32–63% ee, which were converted to chiral 1,2-epithio derivatives.

  用面包酵母处理 α-（二甲基硫代氨基甲酰硫基）酮以高产率和高对映体过量（在大多数情况下，超过 96% ee）提供相应的手性醇。α-（二甲基硫代氨基甲酰硫基）醛被还原为手性 α-（二甲基硫代氨基甲酰硫基）醇，收率 69-92%，ee 为 32-63%，转化为手性 1,2-epithio 衍生物。
• Synthesis of ticagrelor analogues belonging to 1,2,3-triazolo[4,5-d]pyrimidines and study of their antiplatelet and antibacterial activity
  作者：Eric Goffin、Nicolas Jacques、Lucia Musumeci、Alain Nchimi、Cécile Oury、Patrizio Lancellotti、Bernard Pirotte

  DOI：10.1016/j.ejmech.2020.112767

  日期：2020.12

  bactericidal activity against gram-positive bacteria, a series of 1,2,3-triazolo[4,5-d]pyrimidines structurally related to ticagrelor were synthesized and examined as putative antiplatelet and antibacterial agents. The aim was to assess the possibility of dissociating the two biological properties and to find novel 1,2,3-triazolo[4,5-d]pyrimidines expressing antiplatelet activity and devoid of in vitro antibacterial

  基于最近的观察，抗血小板药替卡格雷和其代谢产物之一对革兰氏阳性菌具有杀菌活性，合成并研究了一系列与替卡格雷相关的1,2,3-三唑并[4,5- d ]嘧啶作为推定的抗血小板和抗菌剂。目的是评估解离这两种生物学特性的可能性，并找到表达抗血小板活性且缺乏体外作用的新型1,2,3-三唑并[4,5- d ]嘧啶抗菌活性。合成的新化合物是替卡格雷的已知代谢产物以及结构简化的类似物。发现其中一些表达抗血小板活性并失去抗菌活性，支持了两种活性未必联系在一起的观点。
• TSUBOI, SADAO;KOHARA, NORIYUKI;DOI, KATSUMI;UTAKA, MASANORI;TAKEDA, AKIRA, BULL. CHEM. SOC. JAP., 61,(1988) N 9, C. 3205-3209
  作者：TSUBOI, SADAO、KOHARA, NORIYUKI、DOI, KATSUMI、UTAKA, MASANORI、TAKEDA, AKIRA

  DOI：——

  日期：——
• [EN] TRICYCLIC PYRIDONES AND PYRIMIDONES<br/>[FR] PYRIDONES ET PYRIMIDONES TRICYCLIQUES
  申请人：ERASCA INC

  公开号：WO2021127404A8

  公开（公告）日：2022-08-04
• Preparation and Evaluation of Sulfide Derivatives of the Antibiotic Brefeldin A as Potential Prodrug Candidates with Enhanced Aqueous Solubilities
  作者：Brian M. Fox、Jeffrey A. Vroman、Phillip E. Fanwick、Mark Cushman

  DOI：10.1021/jm010054z

  日期：2001.11.1

  Several sulfide (+)-brefeldin A (BFA) analogues were prepared through the Michael addition of various thiols. Many of the sulfides were also oxidized to the corresponding sulfoxide with m-CPBA. The sulfides were designed to act as BFA prodrugs via the metabolic oxidation to the sulfoxide and subsequent syn elimination. Kinetic experiments were used to prove that the syn elimination of the sulfoxides prepared did in fact take place. Five selenide BFA prodrugs were also prepared that are envisioned to act in the same manner as the sulfides. As expected, when oxidation of the selenide to selenoxide was attempted, in situ syn elimination was observed. All of the compounds prepared were evaluated for antiproliferative activity against human cancer cell lines in the National Cancer Institute screen. The sulfoxides were much more potent than either the sulfides or selenides. Especially notable were sulfoxide 21, which possessed a cytotoxicity mean graph midpoint value (MGM) value lower than BFA itself, and sulfoxide 22, which possessed an MGM value slightly less potent than that of BFA. The sulfide analogues were shown to possess increased aqueous solubilty with respect to BFA.