N-(2-sulfido-1,3,2-oxathiaphospholan-2-yl)benzamide | 722508-21-6

• 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: N-(2-sulfido-1,3,2-oxathiaphospholan-2-yl)benzamide
• 英文别名: N-(2-thiono-1,3,2-oxathiaphospholanyl)benzamide；N-(2-sulfanylidene-1,3,2lambda5-oxathiaphospholan-2-yl)benzamide；N-(2-sulfanylidene-1,3,2λ5-oxathiaphospholan-2-yl)benzamide
• CAS: 722508-21-6
• 化学式: C₉H₁₀NO₂PS₂
• 分子量: 259.29
• InChiKey: FPODDKIJAZMWHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-sulfido-1,3,2-oxathiaphospholan-2-yl)benzamide 在 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 水 、 乙腈 为溶剂， 反应 48.0h， 生成 2',2'-difluoro-2'-deoxycytidine-5'-O-[N-(benzoyl)]phosphoramidate
  参考文献：
  名称：

  N-Acyl-phosphoramidates as potential novel form of gemcitabine prodrugs

  摘要：

  Gemcitabine (dFdC) is a cytidine analog remarkably active against a wide range of solid tumors. Inside a cell, gemcitabine is phosphorylated by deoxycytidine kinase to yield gemcitabine monophosphate, further converted to gemcitabine di- and triphosphate. The most frequent form of acquired resistance to gemcitabine in vitro is the deoxycytidine kinase deficiency. Thus, proper prodrugs carrying the 5'-pdFdC moiety may help to overcome this problem. A series of new derivatives of gemcitabine possessing N-acyl(thio) phosphoramidate moieties were prepared and their cytotoxic properties were determined. N-Acyl-phosphoramidate derivatives of gemcitabine have similar cytotoxicity as gemcitabine itself, and have been found accessible to the cellular enzymes. The nicotinic carboxamide derivative of gemcitabine 5'-O-phosphorothioate occurred to be the best inhibitor of bacterial DNA polymerase I and human DNA polymerase alpha. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.034
• 作为产物：
  描述：

  苯甲酰胺 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 吡啶 为溶剂， 反应 12.0h， 生成 N-(2-sulfido-1,3,2-oxathiaphospholan-2-yl)benzamide
  参考文献：
  名称：

  制备N-酰基磷酰胺基（硫代）（硒代）酸酯的新方法

  摘要：

  制备了羧酰胺的N- [2-（X）-1,3,2-氧代磷杂环戊烷]衍生物（X = S，Se，O），它们与醇的DBU辅助反应生成了相应的O-烷基-N-酰基磷酰胺基（硫代）（硒代）酸酯 通过MS分析，1 H和31 P NMR光谱确认了它们的结构。通过用叔丁基过氧三甲基硅烷处理，独立地将N-酰基磷酰胺基磺酸酯转化为N-酰基磷酰胺基酸酯。氧杂磷腈方法也被用于合成在AMP的5'-OH基团上具有N-脯氨酰磷酰胺基（硫代）（硒代）酸酯键的衍生物。

  DOI：

  10.1016/j.tetlet.2004.04.023

文献信息

• [EN] NOVEL SMALL MOLECULE DRUG CONJUGATES OF GEMCITABINE DERIVATIVES<br/>[FR] NOUVEAUX CONJUGUÉS DE MÉDICAMENTS À PETITES MOLÉCULES DE DÉRIVÉS DE GEMCITABINE
  申请人：EVERETT STEVEN ALBERT

  公开号：WO2019152911A1

  公开（公告）日：2019-08-08

  Disclosed are compounds having formula (I) or a pharmaceutically acceptable salt, ester, amide, solvate, or stereoisomer thereof, wherein L, Y1, Y2, Y3, Y4, Y5, Z1, Z2, Z3, Z4, Z5, Z6, and Effector are each as defined in the specification; compositions thereof; uses thereof; and methods of use thereof.

  本公开涉及具有式（I）的化合物或其药学上可接受的盐、酯、酰胺、溶剂合物或立体异构体，其中L、Y1、Y2、Y3、Y4、Y5、Z1、Z2、Z3、Z4、Z5、Z6和效应物分别如规范中定义；其组合物；其用途；以及其使用方法。
• WO2008/48128
  申请人：——

  公开号：——

  公开（公告）日：——
• 5' O [(N ACYL)AMIDOPHOSPHATE] AND 5' O [(N ACYL)AMIDOTHIOPHOSPHATE] AND 5' O [(N ACYL)AMIDODITHIOPHOSPHATE] AND 5' O [(N ACYL)AMIDOSELENOPHOSPHATE] DERIVATIVES OF NUCLEOSIDES AND PROCESSES FOR THE MANUFACTURE THEREOF
  申请人：Stec Wojciech J.

  公开号：US20100137576A1

  公开（公告）日：2010-06-03

  The subject of the invention includes 5′-O-[(N-acyl)amidophosphate]- and 5′-O-[(N-acyl)amidothiophosphate]- and 5′-O-[(N-acyl)amidodithiophosphate]- and 5′-O-[(N-acyl)amidoselenophosphate]- derivatives of nucleosides.
• NOVEL SMALL MOLECULE DRUG CONJUGATES OF GEMCITABINE DERIVATIVES
  申请人：MaveriX Oncology, Inc.

  公开号：US20210380626A1

  公开（公告）日：2021-12-09

  Disclosed are compounds having formula (I): or a pharmaceutically acceptable salt, ester, amide, solvate, or stereoisomer thereof, wherein L, Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , and Effector are each as defined in the specification; compositions thereof; uses thereof; and methods of use thereof.