3-叠氮基-N-(叔丁基)-5-氯噻吩-2-磺酰胺 | 686271-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 3-叠氮基-N-(叔丁基)-5-氯噻吩-2-磺酰胺
• 英文名称: 3-azido-N-(tert-butyl)-5-chlorothiophene-2-sulfonamide
• 英文别名: 3-azido-N-tert-butyl-5-chlorothiophene-2-sulfonamide
• CAS: 686271-37-4
• 化学式: C₈H₁₁ClN₄O₂S₂
• 分子量: 294.786
• InChiKey: MEZPVPLUWHRSPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-叠氮基-N-(叔丁基)-5-氯噻吩-2-磺酰胺 在 十六烷基三丁基溴化磷 、 sodium tetrahydroborate 、 盐酸 作用下， 生成 3-amino-5-chlorothiophene-2-sulfonamide
  参考文献：
  名称：

  Development of Thiophenic Analogues of Benzothiadiazine Dioxides as New Powerful Potentiators of 2-Amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic Acid (AMPA) Receptors

  摘要：

  On the basis of the results obtained in previous series of AMPA potentiators belonging to 3,4-dihydro-2H-benzo- and 3,4-dihydro-2H-pyrido-1,2,4-thiadiazine 1,1-dioxides, the present work focuses on the design of original isosteric 3,4-dihydro-2H-thieno-1,2,4-thiadiazine 1,1-dioxides. Owing to the sulfur position, three series of compounds were developed and their activity as AMPA potentiators was characterized. In each of the developed series, potent compounds were discovered. After screening the selected active compounds on a safety in vivo test, 6-chloro-4-ethyl-3,4-dihydro-2H-thieno[2,3-e]-1,2,4-thiadiazine 1,1-dioxide (24) appeared as the most promising compound and was further evaluated. Its effects on long-term potentiation in vivo and on AMPA-mediated noradrenaline release were measured to predict its potential cognitive enhancing properties. Finally, an object recognition test performed in mice revealed that 24 was able to significantly enhance cognition, after oral administration, at doses as low as 0.3 mg/kg. This study validates the interest of the isosteric replacement of the benzene or pyridine nuclei by the thiophene nucleus in the ring-fused thiadiazine dioxides class of AMPA potentiators.

  DOI：

  10.1021/jm400676g
• 作为产物：
  描述：

  5-氯-2-噻吩叔丁基磺酰胺 在 仲丁基锂 、 对甲苯磺酰叠氮 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.5h， 生成 3-叠氮基-N-(叔丁基)-5-氯噻吩-2-磺酰胺
  参考文献：
  名称：

  Anti-infective agents

  摘要：

  具有公式1的化合物是丙型肝炎（HCV）聚合酶抑制剂。还公开了一种用于抑制丙型肝炎（HCV）聚合酶的组成和方法，用于制造这些化合物的过程，以及在这些过程中使用的合成中间体。

  公开号：

  US20040087577A1

文献信息

• 6-Chloro-3-alkylamino-4<i>H</i>-thieno[3,2<i>-e</i>]-1,2,4-thiadiazine 1,1-Dioxide Derivatives Potently and Selectively Activate ATP Sensitive Potassium Channels of Pancreatic β-Cells
  作者：Flemming E. Nielsen、Thora B. Bodvarsdottir、Anne Worsaae、Peter MacKay、Carsten E. Stidsen、Harrie C. M. Boonen、Lone Pridal、Per O. G. Arkhammar、Philip Wahl、Lars Ynddal、Finn Junager、Nils Dragsted、Tina M. Tagmose、John P. Mogensen、Anette Koch、Svend P. Treppendahl、J. Bondo Hansen

  DOI：10.1021/jm0208121

  日期：2002.9.1

  6-Chloro-3-alkylamino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide derivatives were synthesized and characterized as activators of adenosine 5'-triphosphate (ATP) sensitive potassium (K-ATP) channels in the beta-cells by measuring effects on membrane potential and insulin release in vitro. The effects on vascular tissue in vitro were measured on rat aorta and small mesenteric vessels. Selected compounds were characterized as competitive inhibitors of [H-3]glibenclamide binding to membranes of HEK293 cells expressing human SUR1/Kir6.2 and as potent inhibitors of insulin release in isolated rat islets. 6-Chloro-3-(1-methylcyclobutyl)amino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (54) was found to bind and activate the SUR1/Kir6.2 KATP channels in the low nanomolar range and to be at least 1000 times more potent than the reference compound diazoxide with respect to inhibition of insulin release from rat islets. Several compounds, e.g., 3-propylamino- (30), 3-isopropylamino- (34), 3-(S)-sec-butylamino- (37), and 3-(1-methylcyclopropyl)amino-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (53), which were found to be potent and beta-cell selective activators of K-ATP channels in vitro, were found to inhibit insulin secretion in rats with minimal effects on blood pressure and to exhibit good oral pharmacokinetic properties.
• ANTI-INFECTIVE AGENTS
  申请人：ABBOTT LABORATORIES

  公开号：EP1560827B1

  公开（公告）日：2010-12-29
• US7425552B2
  申请人：——

  公开号：US7425552B2

  公开（公告）日：2008-09-16
• US7902203B2
  申请人：——

  公开号：US7902203B2

  公开（公告）日：2011-03-08
• [EN] ANTI-INFECTIVE AGENTS<br/>[FR] AGENTS ANTI-INFECTIEUX
  申请人：ABBOTT LAB

  公开号：WO2004041818A1

  公开（公告）日：2004-05-21

  The present invention provides an HCV polymerase inhibiting compound having the formula (I) and a composition comprising a therapeutically effective amount of said compound. The present invention also provides a method for inhibiting hepatitis C virus (HCV) polymerase, a method for inhibiting HCV viral replication, and a method for treating or preventing HCV infection. Processes for making said compounds, and synthetic intermediates employed in said processes, are also provided.