3,3'-[1,4-phenylenebis(sulfinyl)]bispropanoic acid 1,1'-dimethyl ester | 1379507-93-3

• 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: 3,3'-[1,4-phenylenebis(sulfinyl)]bispropanoic acid 1,1'-dimethyl ester
• 英文别名: dimethyl 3,3'-[1,4-phenylenebis(methylenesulfinyl)]dipropanoate；dimethyl 3,3'-[1,4-phenylenebis(methylenesulfinyl)]bispropanoate；1,4-di-{[(2-methoxycarbonylethyl)sulfinyl]methyl}benzene；Methyl 3-[[4-[(3-methoxy-3-oxopropyl)sulfinylmethyl]phenyl]methylsulfinyl]propanoate；methyl 3-[[4-[(3-methoxy-3-oxopropyl)sulfinylmethyl]phenyl]methylsulfinyl]propanoate
• CAS: 1379507-93-3
• 化学式: C₁₆H₂₂O₆S₂
• 分子量: 374.479
• InChiKey: HAOMBSVSYQEIEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,3'-[1,4-phenylenebis(sulfinyl)]bispropanoic acid 1,1'-dimethyl ester 在 氨 、 水 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 48.0h， 生成 1,4-di-{[(β-D-glucopyranosyl)dithio]methyl}benzene
  参考文献：
  名称：

  Synthesis and biological evaluation of a new class of glycoconjugated disulfides that exhibit potential anticancer properties

  摘要：

  A synthetic strategy, based on the in situ generation of sulfenic acids and their thermolysis in the presence of thiols, was developed for obtaining a collection of polyvalent disulfides in which a benzene scaffold accommodates two or three flexible arms connecting saccharide moieties. Targeting carbohydrate metabolism or carbohydrate-binding proteins may constitute important approaches in the discovery process of new therapeutic anticancer agents. Therefore, a preliminary screening to ascertain the cytostatic/cytotoxic potential of this new class of enantiopure glycoconjugated disulfides has been conducted. Among them, products with two disulfide arms, harbouring galactose rings, induced high levels of apoptosis on U937 histiocytic lymphoma cells, but lower levels of cell death on peripheral blood mononuclear cells from healthy donors. Further experiments indicated that apoptosis induced by these glycoconjugated bis(disulfides) in U937 cells corresponds to the Bcl-2-sensitive, intrinsic form of apoptotic cell death. The bioinvestigation was extended to a panel of human cancer cell lines with different levels of malignancy and resistance to chemotherapeutic agents. Compounds under study proved to induce detectable levels of cell death towards all the tested cancer cell lines. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.070
• 作为产物：
  描述：

  1,4-苯二甲硫醇 在 苄基三甲基氢氧化铵 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3,3'-[1,4-phenylenebis(sulfinyl)]bispropanoic acid 1,1'-dimethyl ester
  参考文献：
  名称：

  通过亚磺酸合成氨基官能化两亲分子的双位点反应平台

  摘要：

  描述了一些bolaamphiphiles的合成。这是一种聚合方法，允许将葡糖基衍生物连接到双功能化平台，通过无铜 Sonogashira 交叉耦合。中心核由适当取代的双亚砜与二乙炔基苯的反应获得。这种反应的中间体是容易加到不饱和分子的一个三键上的亚磺基官能团。通过将氨或哌啶亲核加成到分子骨架中已经存在的两个乙烯基磺酰基上，中心核心的功能化为制备更复杂的衍生物开辟了道路。初步理论计算证明并支持了观察到具有意想不到的显着高非对映选择性的新立体碳的形成。两个末端葡糖基部分被有利地去保护以提供氨基官能化的双亲分子。

  DOI：

  10.1039/d2ob01266a

文献信息

• From transient sulfenic acids toward peculiar sulfurated molecules
  作者：Anna Barattucci、Paola Bonaccorsi

  DOI：10.1080/10426507.2016.1252373

  日期：2017.2.1

  contributions on the generation and use of transient sulfenic acids in the stereocontrolled synthesis of sulfoxides and disulfides. These substrates offer a wide range of synthetic opportunities such as the synthesis of sulfinyl dienes to be involved in stereoselective DA reactions, the preparation of libraries of bioactive sulfurated molecules, the synthesis of unsymmetrical disulfides and tripodal sulfoxides

  图形摘要 摘要 亚磺酸 (R-SOH) 经常在生物和合成化学中充当反应性中间体。在大自然为我们提供的众多例子中，半胱氨酸衍生的次磺酸被认为是信号转导、转录调控事件和氧化应激反应的关键中间体。它们还在酶中发挥催化和结构作用。此外，亚磺酸的功能涉及硫代亚磺酸盐的生物合成，硫代亚磺酸盐赋予葱属物种特有的气味和风味，并参与切洋葱的催泪过程。另一方面，它们的 S-O 键的电子性质及其参与各种通常是立体有择的反应，促使次磺酸在有机合成中的许多应用，例如它们用作制备特殊硫化分子的关键中间体。本文旨在总结最近在亚砜和二硫化物立体控制合成中瞬态次磺酸的产生和使用方面的贡献。这些底物提供了广泛的合成机会，例如参与立体选择性 DA 反应的亚磺酰二烯的合成、生物活性硫化分子库的制备、不对称二硫化物和三足亚砜和二硫化物的合成。
• Pyrimidine-derived disulfides as potential antimicrobial agents: synthesis and evaluation <i>in vitro</i>
  作者：Paola Bonaccorsi、Anna Barattucci、Teresa Papalia、Giuseppe Criseo、Caterina Faggio、Orazio Romeo

  DOI：10.1080/17415993.2015.1024679

  日期：2015.5.4
• Sulfenic acid – derived glycoconjugated disulfides and sulfoxides: a biological evaluation on human red blood cells
  作者：Paola Bonaccorsi、Maria Chiara Aversa、Anna Barattucci、Teresa Papalia、Agata Torre、Francesca Trischitta、Caterina Faggio

  DOI：10.1080/17415993.2013.778259

  日期：2013.12.1

  This article examines the effects of some glycoconjugated disulfides and sulfoxides on red blood cells (RBCs). Compounds under study show sugar units connected directly or through a benzene platform, and have been obtained following synthetic pathways based on the sulfenic acid chemistry. In order to evaluate the relationship between the structural features of the thioglycoconjugates under investigation and their potential biological activity, we were interested in assessing both the cytotoxicity and hemolytic activity produced on human RBCs by overnight exposition to the thioglycoconjugates. The absence of both cytotoxic effect and hemolysis produced by the tested compounds on erythrocytes supports the rational design of hemocompatible molecules for biomedical applications.[GRAPHICS].
• Kinetic control in the formation of meso-dithia[3.3]-paracyclophane S,S′-dioxide
  作者：Anna Barattucci、Paola Bonaccorsi、Teresa Papalia、Nadia Manganaro、Giuseppe Gattuso

  DOI：10.1016/j.tetlet.2014.07.082

  日期：2014.9

  meso-(R,S)-Dithia[3.3]-paracyclophane S,S'-dioxide is formed with complete stereoselection by the thermolysis of 3,3'-[1,4-phenylene-bis(methylenesulfinyl)]-dipropanoate-that generates in situ two transient sulfenic acid functions in the presence of p-diethynylbenzene. By employing an improved procedure that we have recently optimized, the title compound has been prepared in a 70% yield as a single diastereoisomer. A density functional B3LYP/6-311+G(d,p) study demonstrates that the final syn-addition cyclization step takes place under kinetic control, through a five-membered transition state that defines the stereochemistry of the resulting cyclophane. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of a new class of glycoconjugated disulfides that exhibit potential anticancer properties
  作者：Paola Bonaccorsi、Francesca Marino-Merlo、Anna Barattucci、Gianluca Battaglia、Emanuela Papaianni、Teresa Papalia、Maria C. Aversa、Antonio Mastino

  DOI：10.1016/j.bmc.2012.03.070

  日期：2012.5

  A synthetic strategy, based on the in situ generation of sulfenic acids and their thermolysis in the presence of thiols, was developed for obtaining a collection of polyvalent disulfides in which a benzene scaffold accommodates two or three flexible arms connecting saccharide moieties. Targeting carbohydrate metabolism or carbohydrate-binding proteins may constitute important approaches in the discovery process of new therapeutic anticancer agents. Therefore, a preliminary screening to ascertain the cytostatic/cytotoxic potential of this new class of enantiopure glycoconjugated disulfides has been conducted. Among them, products with two disulfide arms, harbouring galactose rings, induced high levels of apoptosis on U937 histiocytic lymphoma cells, but lower levels of cell death on peripheral blood mononuclear cells from healthy donors. Further experiments indicated that apoptosis induced by these glycoconjugated bis(disulfides) in U937 cells corresponds to the Bcl-2-sensitive, intrinsic form of apoptotic cell death. The bioinvestigation was extended to a panel of human cancer cell lines with different levels of malignancy and resistance to chemotherapeutic agents. Compounds under study proved to induce detectable levels of cell death towards all the tested cancer cell lines. (C) 2012 Elsevier Ltd. All rights reserved.