S-ethyl O-((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl) carbonothioate | 1121795-67-2

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: S-ethyl O-((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl) carbonothioate
• 英文别名: S-Ethyl O-((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl) carbonothioate；(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ethylsulfanylformate
• CAS: 1121795-67-2
• 化学式: C₈H₁₀O₅S
• 分子量: 218.23
• InChiKey: FNMGIGZFOVYSJH-UHFFFAOYSA-N

物化性质

• 沸点：
  288.2±50.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.1
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  S-ethyl O-((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl) carbonothioate 在 磺酰氯 作用下， 以 DCM 为溶剂， 反应 0.5h， 生成 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl carbonochloridate
  参考文献：
  名称：

  AMINO TRICYCLIC-NUCLEOSIDE COMPOUNDS, COMPOSITIONS, AND METHODS OF USE

  摘要：

  提供的是式（I）的化合物或其药用可接受的盐或溶剂化合物。这些化合物和组合物对治疗由黄病毒科病毒引起的病毒感染有用。

  公开号：

  US20090062223A1
• 作为产物：
  描述：

  4-(羟基甲基)-5-甲基-[1,3]二氧代l-2-酮 、 硫代氯甲酸乙酯 在 吡啶 作用下， 以 乙醚 为溶剂， 反应 17.0h， 以42.2%的产率得到S-ethyl O-((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl) carbonothioate
  参考文献：
  名称：

  [EN] COMBINATION THERAPY FOR HIV WITH ADENOSINE DERIVATIVE AND CAPSID INHIBITORS
  [FR] POLYTHÉRAPIE CONTRE LE VIH COMPRENANT UN DÉRIVÉ D'ADÉNOSINE ET DES INHIBITEURS DE CAPSIDE

  摘要：

  本公开涉及治疗或预防RNA病毒感染和逆转录病毒疾病（如HIV和艾滋病）的方法，包括向需要的受试者施用本文所披露的（a）壳蛋白抑制剂和（b）腺苷衍生物的有效量。还提供了包含有效量的腺苷衍生物和有效量的壳蛋白（CA）抑制剂的组合物。

  公开号：

  WO2022159877A1

文献信息

• AMINO TRICYCLIC-NUCLEOSIDE COMPOUNDS, COMPOSITIONS, AND METHODS OF USE
  申请人：Keicher Jesse Daniel

  公开号：US20090062223A1

  公开（公告）日：2009-03-05

  Provided are compounds of Formula (I) or a pharmaceutically acceptable salt or solvate thereof. The compounds and compositions are useful for treating viral infections caused by the Flaviviridae family of viruses.

  提供的是式（I）的化合物或其药用可接受的盐或溶剂化合物。这些化合物和组合物对治疗由黄病毒科病毒引起的病毒感染有用。
• [EN] PRODRUGS OF GLUTAMINE ANALOGS<br/>[FR] PROMÉDICAMENTS D'ANALOGUES DE GLUTAMINE
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2017023774A9

  公开（公告）日：2017-11-23
• WO2021021717A5
  申请人：——

  公开号：WO2021021717A5

  公开（公告）日：2023-08-07
• [EN] ADENOSINE DERIVATIVE AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME<br/>[FR] DÉRIVÉ D'ADÉNOSINE ET COMPOSITION PHARMACEUTIQUE LE COMPRENANT
  申请人：BRII BIOSCIENCES INC

  公开号：WO2021021717A1

  公开（公告）日：2021-02-04

  Disclosed here is an adenosine derivative prodrug that can have reverse transcriptase inhibitor activity in vivo. This disclosure is also directed to a pharmaceutical composition comprising the adenosine derivative that can be used for the treatment of HIV infection or RNA virus infection.
• Discovery of 6-Diazo-5-oxo-<scp>l</scp>-norleucine (DON) Prodrugs with Enhanced CSF Delivery in Monkeys: A Potential Treatment for Glioblastoma
  作者：Rana Rais、Andrej Jančařík、Lukáš Tenora、Michael Nedelcovych、Jesse Alt、Judson Englert、Camilo Rojas、Anne Le、Amira Elgogary、Jessica Tan、Lenka Monincová、Kelly Pate、Robert Adams、Dana Ferraris、Jonathan Powell、Pavel Majer、Barbara S. Slusher

  DOI：10.1021/acs.jmedchem.6b01069

  日期：2016.9.22

  The glutamine antagonist 6-diazo-5-oxo-l-norleucine (DON, 1) has shown robust anticancer efficacy in preclinical and clinical studies, but its development was halted due to marked systemic toxicities. Herein we demonstrate that DON inhibits glutamine metabolism and provides antitumor efficacy in a murine model of glioblastoma, although toxicity was observed. To enhance DONs therapeutic index, we utilized a prodrug strategy to increase its brain delivery and limit systemic exposure. Unexpectedly, simple alkyl ester-based prodrugs were ineffective due to chemical instability cyclizing to form a unique diazo-imine. However, masking both DONs amine and carboxylate functionalities imparted sufficient chemical stability for biological testing. While these dual moiety prodrugs exhibited rapid metabolism in mouse plasma, several provided excellent stability in monkey and human plasma. The most stable compound (5c, methyl-POM-DON-isopropyl-ester) was evaluated in monkeys, where it achieved 10-fold enhanced cerebrospinal fluid to plasma ratio versus DON. This strategy may provide a path to DON utilization in glioblastoma multiforme patients.