5-叠氮基萘-1-磺酰氯 | 73936-73-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 5-叠氮基萘-1-磺酰氯
• 英文名称: 5-azidonaphthalene-1-sulfonyl chloride
• CAS: 73936-73-9
• 化学式: C₁₀H₆ClN₃O₂S
• 分子量: 267.696
• InChiKey: SMCAJTAQRWSIGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-叠氮基萘-1-磺酰氯 在 一水合肼 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.5h， 以85%的产率得到1-azido-5-naphthalene sulfonyl hydrazide
  参考文献：
  名称：

  10.1080/bbb.58.1013

  摘要：

  DOI：

  10.1080/bbb.58.1013
• 作为产物：
  描述：

  5-叠氮基萘-1-磺酸 在 五氯化磷 作用下， 以44%的产率得到5-叠氮基萘-1-磺酰氯
  参考文献：
  名称：

  Muramoto, Koji; Kamiya, Hisao, Agricultural and Biological Chemistry, 1984, vol. 48, # 11, p. 2695 - 2700

  摘要：

  DOI：

文献信息

• Synthesis of mannopyranose disaccharides as photoaffinity probes for mannosyltransferases in Mycobacterium tuberculosis
  作者：Ashish K Pathak、Vibha Pathak、James M Riordan、Sudagar S Gurcha、Gurdyal S Besra、Robert C Reynolds

  DOI：10.1016/j.carres.2003.10.031

  日期：2004.2

  play a crucial role in mycobacterial cell-wall biosynthesis and are potential new drug targets for the treatment of tuberculosis. Herein, we describe the synthesis of alpha-(1-->2)- and alpha-(1-->6)-linked mannopyranosyl disaccharides possessing a 5-azidonaphthlene-1-sulfonamidoethyl group as photoaffinity probes for active-site labeling studies of mannosyltransferases in Mycobacterium tuberculosis.

  甘露糖基转移酶在分枝杆菌细胞壁生物合成中起关键作用，并且是治疗结核病的潜在新药靶标。在本文中，我们描述了具有5-azidonaphthlene-1-sulfonamidoethyl基的α-（1-> 2）-和alpha-（1-> 6）-连接的甘露吡喃糖基二糖的合成，作为用于活性位点标记研究的光亲和探针结核分枝杆菌中的甘露糖基转移酶的检测
• Synthesis of an arabinofuranosyl disaccharide photoaffinity probe for arabinosyltransferase activity in Mycobacterium tuberculosis
  作者：Ashish K. Pathak、Vibha Pathak、Sudagar S. Gurcha、Gurdyal S. Besra、Robert C. Reynolds

  DOI：10.1016/s0960-894x(02)00536-x

  日期：2002.10

  (5-Azidonaphthalene-1-sulfonamidoethyl)- 5-O-(alpha-arabinofuranosyl)-alpha-D-arabino furano side 1 was synthesized as a photoaffinity probe for the determination of arabinosyl transferase activity and for the identification of binding and functional sites in Mycobacterium tuberculosis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  (5-叠氮萘-1-磺酰氨基乙基)-5-O-(α-L-阿拉伯呋喃核糖基)-α-D-阿拉伯呋喃核苷糖1被合成作为光亲和探针，用于测定阿拉伯糖基转移酶的活性，并用于鉴定在结核分枝杆菌中结合和功能位点。(C)2002 Elsevier Science Ltd. 保留所有权利。
• Novel polyamine analogues as therapeutic and diagnostic agents
  申请人：ORIDIGM CORPORATION

  公开号：EP1085011A1

  公开（公告）日：2001-03-21

  Novel inhibitors of polyamine transport having inhibition constants two orders of magnitude lower than those of known compounds are disclosed. These polyamine analogues are useful pharmaceutical agents for treating disease where it is desired to inhibit polyamine transport or other polyamine binding proteins, for example cancer and post-angioplasty injury. Novel chemical synthetic methods to obtain polyamine analogues are disclosed, including the production of a combinatorial polyamine library. These approaches yield analogues with desirable activities both for diagnostic and research assays and therapy. The assays of the invention are useful for high throughput screening of targets in the discovery of drugs that interact with the polyamine system.

  本发明揭示了具有比已知化合物低两个数量级的抑制常数的多胺转运抑制剂。这些多胺类似物是治疗需要抑制多胺转运或其他多胺结合蛋白的疾病的有用药物，例如癌症和血管成形术后的损伤。揭示了获得多胺类似物的新的化学合成方法，包括制备组合多胺库。这些方法产生的类似物具有理想的诊断和研究测定和治疗活性。本发明的测定方法对于高通量筛选与多胺系统相互作用的药物发现目标非常有用。
• Polyamine analogues as therapeutic and diagnostic agents
  申请人：MediQuest Therapeutics, Inc.

  公开号：EP1867633A1

  公开（公告）日：2007-12-19

  Novel inhibitors of polyamine transport having inhibition constants two orders of magnitude lower than those of known compounds are disclosed. These polyamine analogues are useful pharmaceutical agents for treating diseases where it is desired to inhibit polyamine transport or other polyamine binding proteins, for example cancer and post-angioplasty injury. Novel chemical synthetic methods to obtain polyamine analogues are disclosed, including the production of a combinatorial polyamine library. These approaches yield analogues with desirable activities both for diagnostic and research assays and therapy. The assays of the invention are useful for high throughput screening of targets in the discovery of drugs that interact with the polyamine system.

  本研究公开了新型多胺转运抑制剂，其抑制常数比已知化合物的抑制常数低两个数量级。这些多胺类似物是治疗需要抑制多胺转运或其他多胺结合蛋白的疾病（如癌症和血管成形术后损伤）的有用药物。公开了获得多胺类似物的新型化学合成方法，包括组合多胺库的生产。这些方法产生的类似物具有理想的活性，既可用于诊断和研究测定，也可用于治疗。本发明的检测方法可用于高通量筛选目标，以发现与多胺系统相互作用的药物。
• Disaccharide analogs as probes for glycosyltransferases in Mycobacterium tuberculosis
  作者：Ashish K. Pathak、Vibha Pathak、Lainne Seitz、Sudagar S. Gurcha、Gurdyal S. Besra、James M. Riordan、Robert C. Reynolds

  DOI：10.1016/j.bmc.2007.04.012

  日期：2007.8

  Glycosyltransferases (GTs) play a crucial role in mycobacterial cell wall biosynthesis and are necessary for the survival of mycobacteria. Hence, these enzymes are potential new drug targets for the treatment of tuberculosis (TB), especially multiple drug-resistant TB (MDR-TB). Herein, we report the efficient syntheses of Araf(alpha 1 -> 5)Araf, Ga1f(beta 1 -> 5)Galf and Galf(beta 1 -> 6)Galf disaccharides possessing a 5-N,N-dimethylaminonaphthalene-l-sulfonamidoethyl (dansyl) unit that were prepared as fluorescent disaccharide acceptors for arabinosyl- and galactosyl-transferases, respectively. Such analogs may offer advantages relative to radiolabeled acceptors or donors for studying the enzymes and for assay development and compound screening. Additionally, analogs possessing a 5-azidonaphthalene-1-sulfonamidoethyl unit were prepared as photoaffinity probes for then-potential utility in studying active site labeling of the GTs (arabinosyl and galactosyl) in MYcobacterium tuberculosis (MTB). Beyond their preparation, initial biological testing and kinetic analysis of these disaccharides as acceptors toward glycosyltransferases are also presented. (C) 2007 Elsevier Ltd. All rights reserved.