6-氰基苯并[b]噻吩-2-基硼酸 | 1119899-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 6-氰基苯并[b]噻吩-2-基硼酸
• 英文名称: 6-cyanobenzo[b]thiophen-2-ylboronic acid
• 英文别名: (6-cyanobenzothiophen-2-yl)boronic acid；6-cyanobenzothiophene-2-boronic acid；6-cyanobenzo[b]thiophen-2-yl-2-boronic acid；6-cyanobenzo[b]thiophene-2-boronic acid；6-cyano-benzothiophene-2-boronic acid；(6-Cyanobenzo[b]thiophen-2-yl)boronic acid；(6-cyano-1-benzothiophen-2-yl)boronic acid
• CAS: 1119899-35-2
• 化学式: C₉H₆BNO₂S
• 分子量: 203.029
• InChiKey: MMTVJXZMQSZYDX-UHFFFAOYSA-N

物化性质

• 沸点：
  474.9±48.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.45
• 重原子数：
  14
• 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：
  92.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-溴-5-氟吡啶 、 6-氰基苯并[b]噻吩-2-基硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 生成 2'-(5-fluoro-2-pyridyl)-6-benzo[b]thiophenecarbonitrile
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Botulinum Neurotoxin A Protease Inhibitors

  摘要：

  NSC 240898 was previously identified as a botulinum neurotoxin A light chain (BoNT/A LC) endopeptidase inhibitor by screening the National Cancer Institute Open Repository diversity set. Two types of analogues have been synthesized and shown to inhibit BoNT/A LC in a FRET-based enzyme assay, with confirmation in an HPLC-based assay. These two series of compounds have also been evaluated for inhibition of anthrax lethal factor (LF), an unrelated metalloprotease, to examine enzyme specificity of the BoNT/A LC inhibition. The most potent inhibitor against BoNT/A LC in these two series is compound 12 (IC50 = 2.5 mu M, FRET assay), which is 4.4-fold more potent than the lead structure and 11.2-fold more selective for BoNT/A LC versus the anthrax LF metalloproteinase. Structure-activity relationship studies have revealed structural features important to potency and enzyme specificity.

  DOI：

  10.1021/jm901852f
• 作为产物：
  描述：

  苯并[b]噻吩-6-甲腈 在 正丁基锂 、 硼酸三甲酯 、 盐酸 作用下， 以 四氢呋喃 、 hexanes 、 水 为溶剂， 反应 1.5h， 以72%的产率得到6-氰基苯并[b]噻吩-2-基硼酸
  参考文献：
  名称：

  [EN] PYRROLOPYRIMIDINE COMPOUNDS AND THEIR USE AS JANUS KINASE MODULATORS
  [FR] COMPOSÉS DE PYRROLOPYRIMIDINE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DES JANUS KINASES

  摘要：

  本文提供了通式(I)的吡咯并嘧啶化合物，其中R1是含有至少一个硫原子的杂芳基，并且任选地在芳环碳上被一个、两个或三个取代基取代，这些取代基独立地从以下基团中选择：卤素、羟基、硝基、甲酰基、甲酰胺基、氰基、磺酰基、羧基、氨基、酰胺基、酰氨基、氨基甲酰基、磺酰胺基、烷基、烯基、CF3、脲基、炔基、烷氧基、烷酰基、烷氧羰基、羧醛肟、N-烷基磺酰胺基、N-烷基氨基甲酰基、-OR13R11或-R13R11；R2是苯基或吡啶基，其中R2任选地在环碳上被一个、两个或三个取代基取代，这些取代基独立地从以下基团中选择：卤素、羟基、氰基、硝基、甲酰基、甲酰胺基、羧基、磺酰基、氨基、酰胺基、-N-烷基-氨基、氨基甲酰基、磺酰胺基、CF3、脲基、烷基、烯基、炔基、烷氧基、烷酰基、烷氧羰基、N-烷基磺酰胺基、N-烷基氨基甲酰基、-OR11、-OR12R11或-R12R11；以及其制备和使用方法。这些化合物可用于炎症性或骨髓增生性疾病。该披露还提供了用于治疗癌症的方法。

  公开号：

  WO2009049028A1

文献信息

• [EN] PYRROLOPYRIMIDINE COMPOUNDS AND THEIR USE AS JANUS KINASE MODULATORS<br/>[FR] COMPOSÉS DE PYRROLOPYRIMIDINE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DES JANUS KINASES
  申请人：TARGEGEN INC

  公开号：WO2009049028A1

  公开（公告）日：2009-04-16

  Provided herein are pyrrolopyrimidine compounds of Formula (I) wherein R1 is a heteroaryl containing at least one S atom, and optionally substituted on a ring carbon by one, two, or three substituents each independently selected from the group consisting of : halo, hydroxyl, nitro, formyl, formamido, cyano, sulfonyl, carboxy, amino, amido, acylamino, carbamoyl, sulphamoyl, alkyl, alkenyl, CF3, ureido, alkynyl, alkoxy, alkanoyl, alkoxycarbonyl, carbaldehyde oxime, N -alkylsulphamoyl, N-alkylcarbamoyl, -OR13R11 or -R13R11; R2 is phenyl or pyridinyl, wherein R2 optionally substituted on a ring carbon by one, two, or three substituents each indenpendently selected from the group consisting of : halo, hydroxyl, cyano, nitro, formyl, formamido, carboxy, sulfonyl, amino, amido, -N- alkyl -amino, carbamoyl, sulphamoyl, CF3, ureido, alkyl, alkenyl, alkynyl, alkoxy, alkanoyl, alkoxycarbonyl, N-alkylsulphamoyl, N-alkylcarbamoyl, -OR11, -OR12R11, or -R12R11; and methods of making and using the same. Such compounds may be used in inflammatory or myeloproliferative disorders. The disclosure also provides for treating cancer.

  本文提供了通式(I)的吡咯并嘧啶化合物，其中R1是含有至少一个硫原子的杂芳基，并且任选地在芳环碳上被一个、两个或三个取代基取代，这些取代基独立地从以下基团中选择：卤素、羟基、硝基、甲酰基、甲酰胺基、氰基、磺酰基、羧基、氨基、酰胺基、酰氨基、氨基甲酰基、磺酰胺基、烷基、烯基、CF3、脲基、炔基、烷氧基、烷酰基、烷氧羰基、羧醛肟、N-烷基磺酰胺基、N-烷基氨基甲酰基、-OR13R11或-R13R11；R2是苯基或吡啶基，其中R2任选地在环碳上被一个、两个或三个取代基取代，这些取代基独立地从以下基团中选择：卤素、羟基、氰基、硝基、甲酰基、甲酰胺基、羧基、磺酰基、氨基、酰胺基、-N-烷基-氨基、氨基甲酰基、磺酰胺基、CF3、脲基、烷基、烯基、炔基、烷氧基、烷酰基、烷氧羰基、N-烷基磺酰胺基、N-烷基氨基甲酰基、-OR11、-OR12R11或-R12R11；以及其制备和使用方法。这些化合物可用于炎症性或骨髓增生性疾病。该披露还提供了用于治疗癌症的方法。
• [EN] ANILINOPYRIMIDINES AS JAK KINASE INHIBITORS<br/>[FR] ANILINOPYRIMIDINES EN TANT QU'INHIBITEURS DE KINASES JAK
  申请人：TARGEGEN INC

  公开号：WO2009046416A1

  公开（公告）日：2009-04-09

  Provided herein are pyrimidine compounds, and methods of making and using the same. Such compounds may be used in inflammatory or myeloproliferative disorders. The disclosure also provides for treating cancer.

  本发明提供了嘧啶化合物及其制备和使用方法。这些化合物可用于治疗炎症或骨髓增生性疾病。本发明还提供了治疗癌症的方法。
• Synthesis and antibacterial evaluation of new, unsymmetrical triaryl bisamidine compounds
  作者：Son T. Nguyen、John D. Williams、Michelle M. Butler、Xiaoyuan Ding、Debra M. Mills、Tommy F. Tashjian、Rekha G. Panchal、Susan K. Weir、Chaeho Moon、Hwa-Ok Kim、Jeremiah A. Marsden、Norton P. Peet、Terry L. Bowlin

  DOI：10.1016/j.bmcl.2014.05.094

  日期：2014.8

  is a benzimidazole, imidazopyridine, benzofuran, benzothiophene, pyrimidine or benzene ring. When the [HetAr/Ar] unit is a 5,6-bicyclic heterocycle, it is oriented such that the 5-membered ring portion is connected to the [linker] unit and the 6-membered ring portion is connected to the [Am] unit. Among the 34 compounds in this series, compounds with benzofuran as the [HetAr/Ar] unit showed the highest

  在此，我们描述了一种新型不对称三芳基双脒化合物系列[Am]-[吲哚]-[连接基]-[HetAr/Ar]-[Am]的合成和抗菌评价，其中[Am]是脒或氨基[连接体]为苯环、噻吩环或吡啶环，[HetAr/Ar]为苯并咪唑、咪唑并吡啶、苯并呋喃、苯并噻吩、嘧啶或苯环。[HetAr/Ar]单元为5,6-二环杂环时，其取向为5元环部分与[连接基]单元连接，6元环部分与[Am]连接。单元。在该系列的 34 种化合物中，以苯并呋喃为 [HetAr/Ar] 单元的化合物显示出最高的效力。在三芳基核心中引入氟原子或甲基会产生更有效的类似物。双脒对细菌更具活性，而单脒对哺乳动物细胞更活性（如低 CC 50值所示）。重要的是，我们发现化合物P12a (MBX 1887) 具有相对较窄的抗菌谱和非常高的 CC 50值。化合物P12a已扩大规模，目前正在接受进一步的治疗应用评估。
• Synthesis and antifungal evaluation of head-to-head and head-to-tail bisamidine compounds
  作者：Son T. Nguyen、Steven M. Kwasny、Xiaoyuan Ding、John D. Williams、Norton P. Peet、Terry L. Bowlin、Timothy J. Opperman

  DOI：10.1016/j.bmc.2015.07.006

  日期：2015.9

  Herein, we describe the antifungal evaluation of 43 bisamidine compounds, of which 26 are new, having the scaffold [Am]-[HetAr]-[linker]-[HetAr]-[Am], in which [Am] is a cyclic or acyclic amidine group, [linker] is a benzene, pyridine, pyrimidine, pyrazine ring, or an aliphatic chain of two to four carbon, and [HetAr] is a 5,6-bicyclic heterocycle such as indole, benzimidazole, imidazopyridine, benzofuran, or benzothiophene. In the head-to-head series the two [HetAr] units are oriented such that the 5-membered rings are connected through the linker, and in the head-to-tail series, one of the [HetAr] systems is connected through the 6-membered ring; additionally, in some of the head-to-tail compounds, the [linker] is omitted. Many of these compounds exhibited significant antifungal activity against Candida albicans, Candida krusei, Candida glabrata, Candida parapsilosis, and Cryptococcus neoformans (MIC <= 4 mu g/ml). The most potent compounds, for example, P10, P19 and P34, are comparable in antifungal activities to amphotericin B (MIC 0.125 mu g/ml). They exhibited rapid fungicidal activity (>3 log(10) decrease in cfu/ml in 4 h) at concentrations equivalent to 4x the MIC in time kill experiments. The bisamidines strongly inhibited DNA, RNA and cell wall biosynthesis in C. albicans in macromolecular synthesis assays. However, the half-maximal inhibitory concentration for DNA synthesis was approximately 30-fold lower than those for RNA and cell wall biosynthesis. Fluorescence microscopy of intact cells of C. albicans treated with a bisamidine exhibited enhanced fluorescence in the presence of DNA, demonstrating that the bisamidine was localized to the nucleus. The results of this study show that bisamidines are potent antifungal agents with rapid fungicidal activity, which is likely to be the result of their DNA-binding activity. Although it was difficult to obtain a broad-spectrum antifungal compound with low cytotoxicity, some of the compounds (e.g., P9, P14 and P43) exhibited favorable CC50 values against HeLa cells and maintained considerable antifungal activity. (C) 2015 Elsevier Ltd. All rights reserved.
• [EN] THIAZOLIDINONE COMPOUNDS, AND METHODS OF MAKING AND USING SAME<br/>[FR] COMPOSÉS DE THIAZOLIDINONE ET PROCÉDÉS DE PRÉPARATION ET D'UTILISATION DE CEUX-CI
  申请人：TARGEGEN INC

  公开号：WO2009026345A1

  公开（公告）日：2009-02-26

  Provided herein are thiazolidinone compounds, and methods of making and using the same. Such compounds may be used in inflammatory or immune-mediated disorders. The disclosure provides for treating respiratory or ocular disorders, treating arthritis, or may be used to treat cancer, such as prostate or breast cancer, or multiple myeloma.

  本发明提供了噻唑烷二酮化合物及其制备和使用方法。这类化合物可用于治疗炎症或免疫介导的疾病。本发明可用于治疗呼吸系统或眼部疾病、治疗关节炎，或可用于治疗癌症，如前列腺癌或乳腺癌，或多发性骨髓瘤。