4-isocyanato-benzenesulfonic acid dimethylamide | 20805-57-6

• 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: 4-isocyanato-benzenesulfonic acid dimethylamide
• 英文别名: 4-Isocyanato-N.N-dimethyl-benzolsulfonamid-(1)；4-Isocyanato-benzolsulfonsaeure-dimethylamid；4-Dimethylsulfamoyl-phenylisocyanat；Benzenesulfonamide, 4-isocyanato-N,N-dimethyl-；4-isocyanato-N,N-dimethylbenzenesulfonamide
• CAS: 20805-57-6
• 化学式: C₉H₁₀N₂O₃S
• 分子量: 226.256
• InChiKey: VGKJNJRGKLXWBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  75.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-isocyanato-benzenesulfonic acid dimethylamide 在 盐酸 、 TEA 作用下， 以 1,4-二氧六环 为溶剂， 反应 19.0h， 生成 1-deoxy-1-[6-[[[(4-(N,N-dimethylaminosulfonyl)phenyl)amino]carbonyl]amino]-9H-purin-9-yl]-N-ethyl-β-D-ribofuranuronamide
  参考文献：
  名称：

  新型N6- [4-（取代）磺酰胺基苯基氨基甲酰基]腺苷-5'-尿酰胺作为A3腺苷受体激动剂的合成及生物学评价。

  摘要：

  一系列新的1-脱氧-1-[[（6-（4-（取代-氨基磺酰基）苯基）氨基）羰基氨基-9H-嘌呤-9-基] -N-乙基-β-D-核呋喃核糖酰胺（83-102 ）已合成并在人A3腺苷受体亚型上进行了测试。这项工作中描述的所有衍生物在纳摩尔范围内均表现出与该受体的亲和力，与A1腺苷受体亚型相比具有良好的选择性，证实了对p-磺酰胺基部分对分子的活性有积极影响。发现磺酰胺基核上的最佳取代基是小的烷基，如甲基，异丙基，乙基或烯丙基部分（化合物96-100），而氨基上的单取代导致A3亲和力值降低。当磺酰胺基核心中的氨基由氢化杂环如哌啶，吗啉或吡咯啉表示时，相对于A1腺苷受体亚型的选择性增加。诸如金刚烷和具有四个以上碳原子的烷基链之类的大基团不利于本文所述的A3腺苷受体激动剂的亲和力和选择性。

  DOI：

  10.1021/jm0408161
• 作为产物：
  描述：

  三光气 、 4-氨基-N,N-二甲基苯磺酰胺 在 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 8.5h， 生成 4-isocyanato-benzenesulfonic acid dimethylamide
  参考文献：
  名称：

  Synthesis and structure-activity relationship study of pyrrolidine-oxadiazoles as anthelmintics against Haemonchus contortus

  摘要：

  Parasitic roundworms (nematodes) are significant pathogens of humans and animals and cause substantive socioeconomic losses due to the diseases that they cause. The control of nematodes in livestock animals relies heavily on the use of anthelmintic drugs. However, their extensive use has led to a widespread problem of drug resistance in these worms. Thus, the discovery and development of novel chemical entities for the treatment of parasitic worms of humans and animals is needed. Herein, we describe our medicinal chemistry optimization efforts of a phenotypic hit against Haemonchus contortus based on a pyrrolidine-oxadiazole scaffold. This led to the identification of compounds with potent inhibitory activities (IC50 = 0.78-22.4 mu M) on the motility and development of parasitic stages of H. contortus, and which were found to be highly selective in a mammalian cell counter-screen. These compounds could be used as suitable chemical tools for drug target identification or as lead compounds for further optimization. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112100

文献信息

• Studies on the structure–activity relationship of 1,3,3,4-tetra-substituted pyrrolidine embodied CCR5 receptor antagonists. Part 2: Discovery of highly potent anti-HIV agents
  作者：Ben Li、Eric Dale Jones、Enkun Zhou、Li Chen、Dean Cameron Baylis、Shanghai Yu、Miao Wang、Xing He、Jonathan Alan Victor Coates、David Ian Rhodes、Gang Pei、John Joseph Deadman、Xin Xie、Dawei Ma

  DOI：10.1016/j.bmcl.2010.05.046

  日期：2010.9

  Modification of 1,3,3,4-tetra-substituted pyrrolidine embodied CCR5 receptor antagonists revealed that introducing a fluoro group at the 3-position of the 3-phenyl group to reduce metabolism did not adversely affect the high potency against HIV infection, and that replacing the piperidine ring with a tropane ring could deliver the most potent anti-HIV agents. Stereochemistry of the substituted tropane ring is essential for maintaining the potent anti-HIV activity because only exo-isomers displayed subnanomolar whole cell activity. (C) 2010 Elsevier Ltd. All rights reserved.
• DE750740
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and structure-activity relationship study of pyrrolidine-oxadiazoles as anthelmintics against Haemonchus contortus
  作者：Banfeng Ruan、Yuezhou Zhang、Solomon Tadesse、Sarah Preston、Aya C. Taki、Abdul Jabbar、Andreas Hofmann、Yaqing Jiao、Jose Garcia-Bustos、Jitendra Harjani、Thuy Giang Le、Swapna Varghese、Silvia Teguh、Yiyue Xie、Jephthah Odiba、Min Hu、Robin B. Gasser、Jonathan Baell

  DOI：10.1016/j.ejmech.2020.112100

  日期：2020.3

  Parasitic roundworms (nematodes) are significant pathogens of humans and animals and cause substantive socioeconomic losses due to the diseases that they cause. The control of nematodes in livestock animals relies heavily on the use of anthelmintic drugs. However, their extensive use has led to a widespread problem of drug resistance in these worms. Thus, the discovery and development of novel chemical entities for the treatment of parasitic worms of humans and animals is needed. Herein, we describe our medicinal chemistry optimization efforts of a phenotypic hit against Haemonchus contortus based on a pyrrolidine-oxadiazole scaffold. This led to the identification of compounds with potent inhibitory activities (IC50 = 0.78-22.4 mu M) on the motility and development of parasitic stages of H. contortus, and which were found to be highly selective in a mammalian cell counter-screen. These compounds could be used as suitable chemical tools for drug target identification or as lead compounds for further optimization. (C) 2020 Elsevier Masson SAS. All rights reserved.
• Synthesis and Biological Evaluation of Novel <i>N</i>⁶-[4-(Substituted)sulfonamidophenylcarbamoyl]adenosine-5‘-uronamides as A₃ Adenosine Receptor Agonists
  作者：Pier Giovanni Baraldi、Francesca Fruttarolo、Mojgan Aghazadeh Tabrizi、Romeo Romagnoli、Delia Preti、Andrea Bovero、Maria Josè Pineda de Las Infantas、Allan Moorman、Katia Varani、Pier Andrea Borea

  DOI：10.1021/jm0408161

  日期：2004.10.1

  H-purin-9 -yl]-N-ethyl-beta-D-ribofuranuronamides (83-102) have been synthesized and tested at the human A3 adenosine receptor subtype. All the derivatives described in this work displayed affinity versus this receptor in the nanomolar range and good selectivity versus A1 adenosine receptor subtype, confirming that the p-sulfonamido moiety positively affected the activity of the molecules. The best

  一系列新的1-脱氧-1-[[（6-（4-（取代-氨基磺酰基）苯基）氨基）羰基氨基-9H-嘌呤-9-基] -N-乙基-β-D-核呋喃核糖酰胺（83-102 ）已合成并在人A3腺苷受体亚型上进行了测试。这项工作中描述的所有衍生物在纳摩尔范围内均表现出与该受体的亲和力，与A1腺苷受体亚型相比具有良好的选择性，证实了对p-磺酰胺基部分对分子的活性有积极影响。发现磺酰胺基核上的最佳取代基是小的烷基，如甲基，异丙基，乙基或烯丙基部分（化合物96-100），而氨基上的单取代导致A3亲和力值降低。当磺酰胺基核心中的氨基由氢化杂环如哌啶，吗啉或吡咯啉表示时，相对于A1腺苷受体亚型的选择性增加。诸如金刚烷和具有四个以上碳原子的烷基链之类的大基团不利于本文所述的A3腺苷受体激动剂的亲和力和选择性。