N-hydroxybenzo[b]thiophene-2-carboximidamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: N-hydroxybenzo[b]thiophene-2-carboximidamide
• 英文别名: N'-Hydroxybenzo[b]thiophene-2-carboximidamide；N'-hydroxy-1-benzothiophene-2-carboximidamide
• 化学式: C₉H₈N₂OS
• 分子量: 192.241
• InChiKey: ONPLKPJOVPZABE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-hydroxybenzo[b]thiophene-2-carboximidamide 在 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 xylene 为溶剂， 反应 3.25h， 生成 2-Benzo[b]thiophen-2-yl-5,6-dihydroxypyrimidine-4-carboxylic acid
  参考文献：
  名称：

  2-(2-Thienyl)-5,6-dihydroxy-4-carboxypyrimidines as Inhibitors of the Hepatitis C Virus NS5B Polymerase:  Discovery, SAR, Modeling, and Mutagenesis

  摘要：

  Infections caused by hepatitis C virus (HCV) are a significant world health problem for which novel therapies are in urgent demand. The polymerase of HCV is responsible for the replication of viral RNA. We recently disclosed dihydroxypyrimidine carboxylates 2 as novel, reversible inhibitors of the HCV NS5B polymerase. This series was further developed into 5,6-dihydroxy-2-(2-thienyl)pyrimidine-4-carboxylic acids such as 34 (EC50 9.3 mu M), which now show activity in the cell-based HCV replication assay. The structure-activity relationship of these inhibitors is discussed in the context of their physicochemical properties and of the polymerase crystal structure. We also report the results of mutagenesis experiments which support the proposed binding model, which involves pyrophosphate-like chelation of the active site Mg ions.

  DOI：

  10.1021/jm051064t
• 作为产物：
  描述：

  1-苯并噻酚-2-羧醛 在 甲酸 、 盐酸羟胺 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 25.0h， 生成 N-hydroxybenzo[b]thiophene-2-carboximidamide
  参考文献：
  名称：

  2-(2-Thienyl)-5,6-dihydroxy-4-carboxypyrimidines as Inhibitors of the Hepatitis C Virus NS5B Polymerase:  Discovery, SAR, Modeling, and Mutagenesis

  摘要：

  Infections caused by hepatitis C virus (HCV) are a significant world health problem for which novel therapies are in urgent demand. The polymerase of HCV is responsible for the replication of viral RNA. We recently disclosed dihydroxypyrimidine carboxylates 2 as novel, reversible inhibitors of the HCV NS5B polymerase. This series was further developed into 5,6-dihydroxy-2-(2-thienyl)pyrimidine-4-carboxylic acids such as 34 (EC50 9.3 mu M), which now show activity in the cell-based HCV replication assay. The structure-activity relationship of these inhibitors is discussed in the context of their physicochemical properties and of the polymerase crystal structure. We also report the results of mutagenesis experiments which support the proposed binding model, which involves pyrophosphate-like chelation of the active site Mg ions.

  DOI：

  10.1021/jm051064t

文献信息

• [EN] SPIRO-OXADIAZOLINE COMPOUNDS AS AGONISTS OF α-7-NICOTINIC ACETYLCHOLINE RECEPTORS<br/>[FR] COMPOSÉS SPIRO-OXADIAZOLINE EN TANT QU'AGONISTES DES RÉCEPTEURS DE L'ACÉTYLCHOLINE Α-7 NICOTINIQUE
  申请人：FORUM PHARMACEUTICALS INC

  公开号：WO2015066371A1

  公开（公告）日：2015-05-07

  The present invention relates to novel spiro-oxadiazoline compounds that are suitable as agonists or partial agonists of a7-nAChR, and pharmaceutical compositions of the same, methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering a spiro-oxadiazoline cx7-nAChR agonist or partial agonist, to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.

  本发明涉及新型螺环-噁二唑啉化合物，适用作a7-nAChR的激动剂或部分激动剂，以及这些化合物和组合物的制备方法、药物组合物，以及在维持、治疗和/或改善认知功能的方法中使用这些化合物和组合物。具体而言，涉及向需要的患者（例如患有认知缺陷和/或希望增强认知功能的患者）施用螺环-噁二唑啉cx7-nAChR激动剂或部分激动剂的方法，以使其获益。
• Heterocyclic Compounds and Their Use in the Treatment of Cardiovascular Disease
  申请人：Wang Shouming

  公开号：US20090221564A1

  公开（公告）日：2009-09-03

  Heterocyclic compounds of the formula (I) are provided: wherein ring A, ring B, R 1 , R 2 , R 3 , R 4 , Y, m, n and q are as identified herein. R 1 is in particular amidino. The invention further provides particular benzothiophene compounds. Compounds of the invention may be useful as inhibitors of Factor IXa and in the therapy of cardiovascular conditions and diseases, e.g. thrombosis.

  提供公式（I）的杂环化合物：其中环A、环B、R1、R2、R3、R4、Y、m、n和q如本文所述。 R1特别是氨基亚甲基。该发明还提供特定的苯并噻吩化合物。该发明的化合物可能有助于抑制因子IXa并用于心血管疾病和病症的治疗，例如血栓形成。
• Benzothiazole and benzothiophene derivatives
  申请人：AKZO N.V.

  公开号：EP0158380A1

  公开（公告）日：1985-10-16

  The invention relates to compounds of the general formula I wherein R1 represents one up to and including four, the same or different substituents selected from alkyl (1-6 C), alkoxy (1-6 C), hydroxy, halogen, NO2, CF3 or the group -NR5R6, whereby two substituents taken together may also represent a methylene-dioxy group, X represents nitrogen or the group n has the value 0, 1 or 2, R3 represents one of the moieties: the latter meaning of R3 (amide) only under the condition that for X is nitrogen the meaning of R1 is limited to substituents selected from hydroxy, alkoxy (1-6 C) and methylenedioxy, and R4, R5 and R6 represent hydrogen or alkyl (1-6 C), and pharmaceutically acceptable salts thereof, suitable in the treatment of heart failure.

  本发明涉及通式 I 的化合物 其中 R1 代表一个至四个（包括四个）相同或不同的取代基，选自烷基（1-6 C）、烷氧基（1-6 C）、羟基、卤素、NO2、CF3 或基团 -NR5R6，其中两个取代基组合在一起也可代表亚甲基二氧基基团、 X 代表氮或基团 n 的值为 0、1 或 2、 R3 代表其中一个基团： R3（酰胺）的后一种含义仅限于 X 为氮的条件下，R1 的含义仅限于选自羟基、烷氧基（1-6 C）和亚甲基二氧基的取代基，R4、R5 和 R6 代表氢或烷基（1-6 C），及其药学上可接受的盐，适用于治疗心力衰竭。
• Chloro-oxime derivatives as novel small molecule chaperone amplifiers
  作者：Yuefen Zhou、Khang Vu、Yongsheng Chen、John Pham、Thomas Brady、Gang Liu、Jinhua Chen、Joonwoo Nam、P.S. Murali Mohan Reddy、Qingyan Au、Il Sang Yoon、Marie-Helene Tremblay、Gary Yip、Charmian Cher、Bin Zhang、Jack R. Barber、Shi Chung Ng

  DOI：10.1016/j.bmcl.2009.03.011

  日期：2009.6

  Chloro-oxime derivatives were investigated as novel small molecule chaperone amplifiers. Lead optimization led to the discovery of compounds that displayed potent HSF1 activation activity, significant cytoprotection in MG-132 stress, ER stress and PolyQ stress cell models (EC50 < 10 mu M). (C) 2009 Published by Elsevier Ltd.
• US4665206A
  申请人：——

  公开号：US4665206A

  公开（公告）日：1987-05-12