N-[(1,3-benzothiazol-2-yl)methylidene]hydroxylamine | 1129-05-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: N-[(1,3-benzothiazol-2-yl)methylidene]hydroxylamine
• 英文别名: benzo[b]thiazole-2-carbaldehyde oxime；benzothiazole-2-formaldehyde oxime；benzothiazole-2-carbaldoxime；benzothiazol-2-carbaldoxime；benzothiazole-2-carbaldehyde oxime；Benzothiazol-2-carbaldehyd-oxim；2-Formylbenzothiazole oxime；N-(1,3-benzothiazol-2-ylmethylidene)hydroxylamine
• CAS: 1129-05-1；1199-33-3；1199-34-4
• 化学式: C₈H₆N₂OS
• 分子量: 178.214
• InChiKey: UXIOLCCKLQHTMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 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：
  73.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(1,3-benzothiazol-2-yl)methylidene]hydroxylamine 在 4-nitro-1-((trifluoromethyl)sulfonyl)-1H-imidazole 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以79%的产率得到1,3-苯并噻唑-2-甲腈
  参考文献：
  名称：

  将醛肟转化为腈和异腈的便捷试剂。

  摘要：

  为了用4-硝基-1-（（三氟甲基）磺酰基）-咪唑（NTSI）使醛肟脱羟基，反应条件的轻微改变导致提供腈或异腈的反应路径明显不同。在温和条件下，醛糖肟转化为异腈具有挑战性。

  DOI：

  10.1039/d0cc00188k
• 作为产物：
  描述：

  苯并噻唑-2-甲醛 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以78%的产率得到N-[(1,3-benzothiazol-2-yl)methylidene]hydroxylamine
  参考文献：
  名称：

  [EN] SPIRO-OXADIAZOLINE COMPOUNDS AS AGONISTS OF α-7-NICOTINIC ACETYLCHOLINE RECEPTORS
  [FR] COMPOSÉS SPIRO-OXADIAZOLINE EN TANT QU'AGONISTES DES RÉCEPTEURS DE L'ACÉTYLCHOLINE Α-7 NICOTINIQUE

  摘要：

  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。

  公开号：

  WO2015066371A1

文献信息

• Benzoheterocyclic Oxime Carbamates Active against <i>Mycobacterium tuberculosis</i>: Synthesis, Structure–Activity Relationship, Metabolism, and Biology Triaging
  作者：Renier van der Westhuyzen、Amanda Mabhula、Paul M. Njaria、Rudolf Müller、Denis Ngumbu Muhunga、Dale Taylor、Nina Lawrence、Mathew Njoroge、Christel Brunschwig、Atica Moosa、Vinayak Singh、Srinivasa P.S. Rao、Ujjini H. Manjunatha、Paul W. Smith、Digby F. Warner、Leslie J. Street、Kelly Chibale

  DOI：10.1021/acs.jmedchem.1c00707

  日期：2021.7.8

  microsomes and no hERG channel inhibition liability were identified and evaluated in vivo for pharmacokinetic properties. Mtb-mediated permeation and metabolism studies revealed that the carbamates were acting as prodrugs. Toward mechanism of action elucidation, selected compounds were tested in biology triage assays to assess their activity against known promiscuous targets. Taken together, these data suggest

  筛选抗结核分枝杆菌( Mtb )的小极性分子文库，鉴定了有效的苯并杂环肟氨基甲酸酯系列。该系列经历了以构效关系研究为基础的药物化学进展，以确定用于概念验证研究的化合物并定义先导优化策略。在肝微粒体中具有良好稳定性且无 hERG 通道抑制倾向的氨基甲酸酯和游离肟领先化合物被鉴定并在体内评估了药代动力学特性。山地车介导的渗透和代谢研究表明氨基甲酸酯充当前药。为了阐明作用机制，在生物学分类试验中测试了选定的化合物，以评估它们对已知混杂靶标的活性。综上所述，这些数据表明这些抗结核药物有一种新颖但未知的作用模式。
• 一种苯并噻唑-噁唑型α-葡萄糖苷酶抑制剂及 其制备方法和应用
  申请人：贵州医科大学

  公开号：CN108530438B

  公开（公告）日：2020-12-29

  本发明公开了一种苯并噻唑‑噁唑型α‑葡萄糖苷酶抑制剂及制备方法。该方法包括：化合物(II)和盐酸羟胺加入甲醇水溶液和碳酸钠水溶液反应得到的化合物(III)；化合物(III)与锌粉、甲酸铵加入甲醇反应后得到化合物(IV)；化合物(IV)与化合物(V)、碘、碳酸钾加入DMF反应后得化合物(I)；化合物(I)的化学式为化合物(II)的化学式为化合物(III)的化学式为化合物(IV)的化学式为化合物(V)的化学式为本发明苯并噻唑‑噁唑型化合物对α‑葡萄糖苷酶具有明显的抑制作用，制备方法简单，反应条件温和，适合大规模工业化生产。
• Synthesis of heterocyclic N-(β-d-glucopyranosyl)carboxamides for inhibition of glycogen phosphorylase
  作者：Bálint Kónya、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.carres.2012.01.020

  日期：2012.4

  In a DCC-mediated coupling 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamine and propiolic acid gave N-propynoyl-2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosylamine which was transformed by 1,3-dipolar cycloadditions with aromatic azides and nitrile-oxides to the corresponding O-peracetylated N-(beta-D-glucopyranosyl)-1-substituted-1,2,3-triazole-4-carboxamides and N-(beta-D-glucopyranosyl)-3-substitutedisoxazole-5-carboxamides, respectively. These compounds were O-deacetylated by Zemplen's protocol to be tested as inhibitors of rabbit muscle glycogen phosphorylase b. The best inhibitors of the two series were N-(beta-D-glucopyranosyl)-1-(3,5-dimethyl-phenyl)-1,2,3-triazole-4-carboxamide (K-i = 34 mu M) and N-(beta-D-glucopyranosyl)-3-(indol-2-yl)-isoxazole-5-carboxamide (K-i = 164 mu M). (C) 2012 Elsevier Ltd. All rights reserved.
• Glucose-derived spiro-isoxazolines are anti-hyperglycemic agents against type 2 diabetes through glycogen phosphorylase inhibition
  作者：David Goyard、Bálint Kónya、Aikaterini S. Chajistamatiou、Evangelia D. Chrysina、Jérémy Leroy、Sophie Balzarin、Michel Tournier、Didier Tousch、Pierre Petit、Cédric Duret、Patrick Maurel、László Somsák、Tibor Docsa、Pál Gergely、Jean-Pierre Praly、Jacqueline Azay-Milhau、Sébastien Vidal

  DOI：10.1016/j.ejmech.2015.12.004

  日期：2016.1

  Glycogen phosphorylase (GP) is a target for the treatment of hyperglycaemia in the context of type 2 diabetes. This enzyme is responsible for the depolymerization of glycogen into glucose thereby affecting the levels of glucose in the blood stream. Twelve new D-glucopyranosylidene-spiro-isoxazolines have been prepared from O-peracylated exo-D-glucals by regio- and stereoselective 1,3-dipolar cycloaddition of nitrile oxides generated in situ by treatment of the corresponding oximes with bleach. This mild and direct procedure appeared to be applicable to a broad range of substrates. The corresponding 0-unprotected spiro-isoxazolines were evaluated as glycogen phosphorylase (GP) inhibitors and exhibited IC50 values ranging from 1 to 800 mu M. Selected inhibitors were further evaluated in vitro using rat and human hepatocytes and exhibited significant inhibitory properties in the primary cell culture. Interestingly, when tested with human hepatocytes, the tetra-O-acetylated spiro-isoxazoline bearing a 2-naphthyl residue showed a much lower IC50 value (2.5 mu M), compared to that of the 0-unprotected analog (19.95 mu M). The most promising compounds were investigated in Zucker fa/fa rat model in acute and sub-chronic assays and decreased hepatic glucose production, which is known to be elevated in type 2 diabetes. This indicates that glucose-based spiro-isoxazolines can be considered as anti-hyperglycemic agents in the context of type 2 diabetes. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Synthesis of C-xylopyranosyl- and xylopyranosylidene-spiro-heterocycles as potential inhibitors of glycogen phosphorylase
  作者：László Somsák、Éva Bokor、Beáta Czibere、Katalin Czifrák、Csenge Koppány、László Kulcsár、Sándor Kun、Enikő Szilágyi、Marietta Tóth、Tibor Docsa、Pál Gergely

  DOI：10.1016/j.carres.2014.05.020

  日期：2014.11

  New derivatives of D-xylose with aglycons of the most efficient glucose derived inhibitors of glycogen phosphorylase were synthesized to explore the specificity of the enzyme towards the structure of the sugar part of the molecules. Thus, 2-(beta-D-xylopyranosyl) benzimidazole and 3-substituted-5-(beta-D-xylopyranosyl)1,2,4-triazoles were obtained in multistep procedures from O-perbenzoylated b-D-xylopyranosyl cyanide. Cycloadditions of nitrile-oxides and O-peracetylated exo-xylal obtained from the corresponding beta-D-xylopyranosyl cyanide furnished xylopyranosylidene-spiro-isoxazoline derivatives. Oxidative ring closure of O-peracetylated beta-D-xylopyranosyl-thiohydroximates prepared from 1-thio-beta-D-xylopyranose and nitrile-oxides gave xylopyranosylidene-spiro-oxathiazoles. The fully deprotected test compounds were assayed against rabbit muscle glycogen phosphorylase b to show moderate inhibition for 3-(2-naphthyl)-5-(beta-D-xylopyranosyl)-1,2,4-triazole (IC50 = 0.9 mM) only. (C) 2014 Elsevier Ltd. All rights reserved.