ethyl 1-naphthylsulfonylcarbamate | 391681-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 1-naphthylsulfonylcarbamate
• 英文别名: ethyl N-naphthalen-1-ylsulfonylcarbamate
• CAS: 391681-03-1
• 化学式: C₁₃H₁₃NO₄S
• 分子量: 279.317
• InChiKey: JUQCJZSMJOLCHG-UHFFFAOYSA-N

物化性质

• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-naphthylsulfonylcarbamate 在 盐酸 、 三乙胺 作用下， 以 甲苯 为溶剂， 以86%的产率得到methyl 5,6-dihydroxy-2-[4-(1-naphthylsulfonylaminocarbonylamino)thien-3-yl]pyrimidine-4-carboxylate
  参考文献：
  名称：

  Dihydroxypyrimidine carboxylic acids as viral polymerase inhibitors

  摘要：

  2-芳基-4,5-二羟基-6-羧基嘧啶的一类化合物的化学式(I)：其中Ar是一个可选择地取代的芳基或杂环基；以及在4-羟基、5-羟基或6-羧基中的一个或多个位置衍生的化合物的化学式(I)；以及它们的互变异构体，以及它们的药用盐或酯；以及病毒聚合酶抑制剂，特别是乙型肝炎病毒（HCV）聚合酶酶。

  公开号：

  US20040106627A1
• 作为产物：
  描述：

  1-萘磺酰胺 、 氯甲酸乙酯 在 potassium carbonate 作用下， 生成 ethyl 1-naphthylsulfonylcarbamate
  参考文献：
  名称：

  Novel agents effective against solid tumors: the diarylsulfonylureas. Synthesis, activities, and analysis of quantitative structure-activity relationships

  摘要：

  A series of diarylsulfonylureas with exceptionally broad-spectrum activity against syngeneic rodent solid tumors in vivo is described. Their discovery resulted from a program dedicated to in vivo screening for novel oncolytics in solid tumor models, rather than traditional ascites leukemia models. The structures, oral efficacy, side-effect profile, and mechanism of action of these sulfonylureas appear to be distinct from previously known classes of oncolytics. An extensive series of analogues was prepared to probe structure-activity relationships (SAR), with particular focus on the substituent patterns of each aryl domain. Quantitative analysis of these substituent SARs, using the method of cluster significance analysis, showed the lipophilicity of the substituents to be the dominant determinant of activity. One compound from the series, LY186641 (104, sulofenur), has progressed to Phase I clinical trials as an antitumor drug.

  DOI：

  10.1021/jm00171a013

文献信息

• Arylsulfonylacetamides as bifunctional reagents for alkene aminoarylation
  作者：Timothy M. Monos、Rory C. McAtee、Corey R. J. Stephenson

  DOI：10.1126/science.aat2117

  日期：2018.9.28

  process, single-electron alkene oxidation enables carbon-nitrogen bond formation to provide a key benzylic radical poised for a Smiles-Truce 1,5-aryl shift. This reaction is redox-neutral, exhibits broad functional group compatibility, and occurs at room temperature with loss of sulfur dioxide. As this process is driven by visible light, uses readily available starting materials, and demonstrates convergent

  来自单一来源的芳烃和酰胺药物合成通常需要形成相邻的碳-碳和碳-氮键。莫诺斯等人。提出了一种将碳和氮组分传递到单一试剂中的方法，特别是通过二氧化硫连接到酰胺的芳基环。光活化催化剂引发烯烃与氮反应，进而导致芳基环迁移和硫桥损失。高效的室温工艺适用于各种不同的芳烃，包括杂环。科学，本期第 3 页。1369 Photoredox 催化激活烯烃通过与单一试剂偶联形成相邻的 C-C 和 C-N 键。使用单一双功能试剂进行烯烃氨基芳基化是一种简洁的合成策略。我们报告了一种催化方案，用于在富电子烯烃中添加芳基磺酰乙酰胺，具有完全的抗马尔科夫尼科夫区域选择性和出色的非对映选择性，以提供 2,2-二芳基乙胺。在这个过程中，单电子烯烃氧化能够形成碳-氮键，从而为 Smiles-Truce 1,5-芳基位移提供关键的苄基自由基。该反应是氧化还原中性的，表现出广泛的官能团相容性，并且在室温下发生并损失二氧化硫。由于
• Dihydroxypyridmidine carboxylic acids as viral polymerase inhibitors
  申请人：Merck & Co., Inc.

  公开号：US07091209B2

  公开（公告）日：2006-08-15

  A class of 2-aryl-4,5-dihydroxy-6-carboxypyrimidines of formula (I): wherein Ar is an optionally substituted aryl or heterocyclicgroup; as well as compounds of formula (I) which are derivatized at one or more of the 4-hydroxy, 5-hydroxy or 6-carboxy groups; and tautomers thereof, and pharmaceutically acceptable salts or esters thereof; and inhibitors of viral polymerases, especially the hepatitis C virus (HCV) polymerase enzyme

  一类化合物的化学式为(I)的2-芳基-4,5-二羟基-6-羧基嘧啶，其中Ar是可选取代的芳基或杂环基；以及在4-羟基，5-羟基或6-羧基中的一个或多个位置上衍生的化合物的化学式(I)；它们的互变异构体和其药学上可接受的盐或酯；以及用于抑制病毒聚合酶，特别是丙型肝炎病毒（HCV）聚合酶酶的抑制剂。
• DIHYDROXYPYRIMIDINE CARBOXYLIC ACIDS AS VIRAL POLYMERASE INHIBITORS
  申请人：ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.

  公开号：EP1309566A1

  公开（公告）日：2003-05-14
• US7091209B2
  申请人：——

  公开号：US7091209B2

  公开（公告）日：2006-08-15
• [EN] DIHYDROXYPYRIMIDINE CARBOXYLIC ACIDS AS VIRAL POLYMERASE INHIBITORS<br/>[FR] ACIDES CARBOXYLIQUES DE DIHYDROXYPYRIMIDINE UTILISES COMME INHIBITEURS DE POLYMERASES VIRALES
  申请人：ANGELETTI P IST RICHERCHE BIO

  公开号：WO2002006246A1

  公开（公告）日：2002-01-24

  A class of 2-aryl-4, 5-dihydroxy-6-carboxypyrimidines of formula (I): wherein Ar is an optionally substituted aryl or heterocyclicgroup; as well as compounds of formula (I) which are derivatised at one or more of the 4-hydroxy, 5-hydroxy or 6-carboxy groups; and tautomers thereof, and pharmaceutically acceptable salts or esters thereof; and inhibitors of viral polymerases, especially thehepatitis C virus (HCV) polymerase enzyme.