S-1,3-di-O-(para-toluenesulfonyl)butane | 74044-83-0

• 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: S-1,3-di-O-(para-toluenesulfonyl)butane
• 英文别名: (S)-1,3-ditosyloxybutane；S-1,3-di-O-p-toluenesulfonyl-butane；[(3S)-3-(4-methylphenyl)sulfonyloxybutyl] 4-methylbenzenesulfonate
• CAS: 74044-83-0
• 化学式: C₁₈H₂₂O₆S₂
• 分子量: 398.501
• InChiKey: YSOXTCSGMGOBKU-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  sodium cyanide 、 S-1,3-di-O-(para-toluenesulfonyl)butane 以 二甲基亚砜 为溶剂， 反应 18.0h， 生成 S-3-O-p-toluenesulfonyl-pentanenitrile
  参考文献：
  名称：

  Cytotoxic agents comprising new maytansinoids

  摘要：

  揭示了具有α-碳原子上带有硫原子的单烷基或双烷基取代基的新硫醇和二硫化物含有马坦西诺伊德。还公开了合成这些新马坦西诺伊德的方法以及将这些新马坦西诺伊德连接到细胞结合剂的方法。马坦西诺伊德-细胞结合剂结合物可用作治疗剂，专门传递到靶细胞并具有细胞毒性。与先前描述的药物相比，这些结合物在动物肿瘤模型中显示出大大改善的治疗效果。

  公开号：

  US20040235840A1
• 作为产物：
  描述：

  (S)-(+)-1,3-丁二醇 在 吡啶 作用下， 生成 S-1,3-di-O-(para-toluenesulfonyl)butane
  参考文献：
  名称：

  Kagan,H.B. et al., Bulletin des Societes Chimiques Belges, 1979, vol. 88, p. 923 - 931

  摘要：

  DOI：

文献信息

• [EN] TOPOISOMERASE POISONS<br/>[FR] POISONS DE TOPOISOMÉRASE
  申请人：UNIV RUTGERS

  公开号：WO2017176648A1

  公开（公告）日：2017-10-12

  Provided herein are compounds of formula (I): and salts thereof. Also provided are pharmaceutical compositions comprising a compound of formula (I), processes for preparing compounds of formula (I), intermediates useful for preparing compounds of formula (I), and therapeutic methods for treating diseases such as cancer, a bacterial infection or a fungal infection using compounds of formula (I).

  本文提供的是式(I)的化合物及其盐。还提供了包括式(I)的化合物的药物组合物，制备式(I)的化合物的方法，制备式(I)的有用中间体，以及使用式(I)的化合物治疗疾病（如癌症、细菌感染或真菌感染）的治疗方法。
• CYTOTOXIC AGENTS COMPRISING NEW MAYTANSINOIDS
  申请人：Chari V. J. Ravi

  公开号：US20070264266A1

  公开（公告）日：2007-11-15

  New thiol and disulfide-containing maytansinoids bearing a mono or di-alkyl substitution on the α-carbon atom bearing the sulfur atom are disclosed. Also disclosed are methods for the synthesis of these new maytansinoids and methods for the linkage of these new maytansinoids to cell-binding agents. The maytansinoid-cell-binding agent conjugates are useful as therapeutic agents, which are delivered specifically to target cells and are cytotoxic. These conjugates display vastly improved therapeutic efficacy in animal tumor models compared to the previously described agents.

  公开了一种新的含有巯基和二硫键的马丹霉素衍生物，其α-碳原子上带有硫原子的位置上具有单烷基或双烷基取代。还公开了制备这些新马丹霉素衍生物的方法以及将这些新马丹霉素衍生物与细胞结合剂连接的方法。马丹霉素-细胞结合剂共轭物作为治疗剂具有特异性地传递到目标细胞并具有细胞毒性。与先前描述的药物相比，这些共轭物在动物肿瘤模型中显示出极大的治疗效果。
• CYTOTOXIC AGENTS COMPRISING NEW MAYTANSINOIDS (DM4)
  申请人：ImmunoGen, Inc.

  公开号：US20150071949A1

  公开（公告）日：2015-03-12

  New thiol and disulfide-containing maytansinoids bearing a mono or di-alkyl substitution on the α-carbon atom bearing the sulfur atom are disclosed. Also disclosed are methods for the synthesis of these new maytansinoids and methods for the linkage of these new maytansinoids to cell-binding agents. The maytansinoid-cell-binding agent conjugates are useful as therapeutic agents, which are delivered specifically to target cells and are cytotoxic. These conjugates display vastly improved therapeutic efficacy in animal tumor models compared to the previously described agents.

  本文介绍了一种新的含巯基和二硫键的马丹霉素衍生物，其α-碳原子上的硫原子带有单烷基或双烷基取代基。同时，还揭示了合成这些新马丹霉素衍生物和将其与细胞结合剂连接的方法。马丹霉素-细胞结合剂结合物可作为治疗剂，专门传递到靶细胞并具有细胞毒性。与先前描述的治疗剂相比，这些结合物在动物肿瘤模型中显示出极大的治疗效果。
• Access to (S)-2-methyloxetane and the precursor (S)-1,3-butanediol of high enantiomeric purity
  作者：Klaus Hintzer、Bernhard Koppenhoefer、Volker Schurig

  DOI：10.1021/jo00141a009

  日期：1982.9
• Semisynthetic Maytansine Analogues for the Targeted Treatment of Cancer
  作者：Wayne C. Widdison、Sharon D. Wilhelm、Emily E. Cavanagh、Kathleen R. Whiteman、Barbara A. Leece、Yelena Kovtun、Victor S. Goldmacher、Hongsheng Xie、Rita M. Steeves、Robert J. Lutz、Robert Zhao、Lintao Wang、Walter A. Blättler、Ravi V. J. Chari

  DOI：10.1021/jm060319f

  日期：2006.7.1

  Maytansine, a highly cytotoxic natural product, failed as an anticancer agent in human clinical trials because of unacceptable systemic toxicity. The potent cell killing ability of maytansine can be used in a targeted delivery approach for the selective destruction of cancer cells. A series of new maytansinoids, bearing a disulfide or thiol substituent were synthesized. The chain length of the ester side chain and the degree of steric hindrance on the carbon atom bearing the thiol substituent were varied. Several of these maytansinoids were found to be even more potent in vitro than maytansine. The targeted delivery of these maytansinoids, using monoclonal antibodies, resulted in a high, specific killing of the targeted cells in vitro and remarkable antitumor activity in vivo.