methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate | 1206907-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate
• CAS: 1206907-38-1
• 化学式: C₉H₇BrN₂O₂S
• 分子量: 287.137
• InChiKey: ICWOLCSNJJNKMP-UHFFFAOYSA-N

物化性质

• 熔点：
  157-159 °C
• 沸点：
  409.6±40.0 °C(Predicted)
• 密度：
  1.765±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate 在 copper(l) chloride 、 copper dichloride 、 亚硝酸特丁酯 作用下， 以 乙腈 为溶剂， 反应 3.17h， 以71%的产率得到methyl 6-bromo-3-chlorothieno[3,2-b]pyridine-2-carboxylate
  参考文献：
  名称：

  [EN] SUBSTITUTED 1,1'-BIPHENYL COMPOUNDS AND METHODS USING SAME
  [FR] COMPOSÉS 1,1'-BIPHÉNYLE SUBSTITUÉS ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  本发明包括取代的1,1'-联苯化合物，其类似物，以及包含它们的组合物。在一个方面，本发明中考虑的化合物可用于治疗、改善或预防患者体内的乙型肝炎病毒（HBV）和/或丙型肝炎病毒（HDV）感染。在另一个方面，本发明中考虑的化合物可用于治疗、改善和/或预防患者体内的癌症。

  公开号：

  WO2021158481A1
• 作为产物：
  描述：

  5-溴-2-氰基-3-硝基吡啶 、 巯基乙酸甲酯 在 potassium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以90%的产率得到methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate
  参考文献：
  名称：

  钯催化偶联和分子内环化反应合成新的噻吩并[3,2- b ]吡啶衍生物

  摘要：

  两个甲基3-氨基噻吩并[3,2- b ]吡啶-2-羧酸盐是从3制备-氟或3- nitropicolinonitriles和巯基乙酸甲酯在DMF / KOH（水溶液）。从吡啶环中未取代的前体中，通过C–N Buchwald–Hartwig与溴硝基苯和2-溴吡啶的偶联，获得二（杂）芳基胺。在后一种情况下，通过分子内环化形成四环化合物。使用吡啶环中的溴化衍生物作为偶联成分，可以合成C–C（Suzuki和Sonogashira）和C–N（Buchwald–Hartwig）偶联产物，以及通过噻吩并吡啶系统双官能化获得的四环化合物。

  DOI：

  10.1016/j.tetlet.2009.10.138

文献信息

• FURO- AND THIENO-PYRIDINE CARBOXAMIDE COMPOUNDS USEFUL AS PIM KINASE INHIBITORS
  申请人：Incyte Corporation

  公开号：US20150057265A1

  公开（公告）日：2015-02-26

  The present disclosure describes furo- and thieno-pyridine carboxamide compounds, as well as their compositions and methods of use. The compounds inhibit the activity of the Pim kinases, and are useful in the treatment of diseases related to the activity of Pim kinases including, e.g., cancer and other diseases.

  本公开描述了呋喃和噻吩吡啶羧酰胺化合物，以及它们的组合物和使用方法。这些化合物抑制Pim激酶的活性，并且在治疗与Pim激酶活性相关的疾病方面具有用处，例如癌症和其他疾病。
• Crystal Structure-Guided Design of Bisubstrate Inhibitors and Photoluminescent Probes for Protein Kinases of the PIM Family
  作者：Olivier E. Nonga、Darja Lavogina、Erki Enkvist、Katrin Kestav、Apirat Chaikuad、Sarah E. Dixon-Clarke、Alex N. Bullock、Sergei Kopanchuk、Taavi Ivan、Ramesh Ekambaram、Kaido Viht、Stefan Knapp、Asko Uri

  DOI：10.3390/molecules26144353

  日期：——

  complexes of protein kinase PIM-1 with three inhibitors comprising an adenosine mimetic moiety, a linker, and a peptide-mimetic (d-Arg)6 fragment. Guided by the structural models, simplified chemical structures with a reduced number of polar groups and chiral centers were designed. The developed inhibitors retained low-nanomolar potency and possessed remarkable selectivity toward the PIM kinases. The new

  我们对蛋白激酶 PIM-1 与三种抑制剂的复合物进行了 X 射线晶体学研究，包括腺苷模拟物部分、接头和肽模拟物 ( d -Arg) 6分段。在结构模型的指导下，设计了极性基团和手性中心数量减少的简化化学结构。开发的抑制剂保留了低纳摩尔的效力，并对 PIM 激酶具有显着的选择性。新抑制剂用生物素或荧光染料 Cy5 衍生化，然后用于检测生化溶液和复杂生物样品中的 PIM 激酶。利用 PIM-2 选择性检测抗体的夹心分析具有低定量限（44 pg 活性重组 PIM-2）。荧光探针被 U2OS 细胞有效吸收，并显示出与融合了荧光蛋白的 PIM-1 的高度共定位。总体，
• Furo- and thieno-pyridine carboxamide compounds useful as pim kinase inhibitors
  申请人：Incyte Corporation

  公开号：US10000507B2

  公开（公告）日：2018-06-19

  The present disclosure describes furo- and thieno-pyridine carboxamide compounds, as well as their compositions and methods of use. The compounds inhibit the activity of the Pim kinases, and are useful in the treatment of diseases related to the activity of Pim kinases including, e.g., cancer and other diseases.

  本公开描述了呋喃和噻吩吡啶羧酰胺化合物及其组合物和使用方法。这些化合物抑制 Pim 激酶的活性，可用于治疗与 Pim 激酶活性有关的疾病，包括癌症和其他疾病。
• Synthesis and evaluation of tumor cell growth inhibition of methyl 3-amino-6-[(hetero)arylethynyl]thieno[3,2-b]pyridine-2-carboxylates. Structure–activity relationships, effects on the cell cycle and apoptosis
  作者：Maria-João R.P. Queiroz、Ricardo C. Calhelha、Luís A. Vale-Silva、Eugénia Pinto、Gabriela M. Almeida、M. Helena Vasconcelos

  DOI：10.1016/j.ejmech.2010.11.009

  日期：2011.1

  The methyl 3-amino-6-bromothieno[3,2-b]pyridine-2-carboxylate, recently reported by some of us, was reacted in Sonogashira couplings with several (hetero)arylacetylenes. The growth inhibitory activity of the novel methyl 3-amino-6-[(hetero)arylethynyl]thieno[3,2-b]pyridine-2-carboxylates obtained was evaluated on three human tumor cell lines (MCF-7, NCI-H460, A375-C5). The para-methoxyphenyl and the ortho- and para-aminophenyl derivatives were the most promising compounds, and their effects were further studied regarding alterations in the normal cell cycle distribution and induction of apoptosis in the NCI-H460 cell line. All three compounds altered cell cycle distribution and the ortho-aminophenyl derivative was further shown to induce apoptosis in the same cell line. (C) 2010 Elsevier Masson SAS. All rights reserved.
• New 1,3-diarylureas linked by CC Suzuki coupling to the methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate moiety: Synthesis and fluorescence studies in solution and in lipid membranes
  作者：Maria-João R.P. Queiroz、Daniela Peixoto、Ana Rita O. Rodrigues、Pedro M.F. Mendes、Cátia N.C. Costa、Paulo J.G. Coutinho、Elisabete M.S. Castanheira

  DOI：10.1016/j.jphotochem.2013.01.006

  日期：2013.3

  New six fluorescent 1,3-diarylureas linked by C-C Suzuki coupling to the 6-position of the methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate moiety were prepared by reaction of the amino groups on the ortho or meta positions relative to the C-C bond of the Suzuki coupling products, with different para-substituted arylisocyanates (H, OMe, CN), in high to excellent yields. The fluorescence properties of the 1,3-diarylureas in solution and in lipid membranes of egg yolk phosphatidylcholine (Egg-PC), dipalmitoyl phosphatidylcholine (DPPC), dipalmitoyl phosphatidylglycerol (DPPG) or dioctadecyldimethylammonium bromide (DODAB), with or without cholesterol (Ch), were studied. The six 1,3-diarylureas have reasonable fluorescence quantum yields in several solvents (0.02 <= Phi(F) <= 0.69) and present a moderately solvent sensitive emission, but are not fluorescent in alcohols and water. The compounds bearing the arylurea moiety in the meta position relative to the C-C bond, especially with the OMe and CN substituents, present the better solvatochromic properties.Incorporation of the six compounds in lipid membranes indicates that all the compounds are deeply located in the hydrophobic region of the lipid bilayers, feeling the transition between the rigid gel phase and fluid phases. (C) 2013 Elsevier B.V. All rights reserved.