pyridin-2-yl(thiophen-3-yl)methanone | 21327-68-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: pyridin-2-yl(thiophen-3-yl)methanone
• CAS: 21327-68-4
• 化学式: C₁₀H₇NOS
• 分子量: 189.238
• InChiKey: ZPXHTXFEGJRBGA-UHFFFAOYSA-N

物化性质

• 沸点：
  170-180 °C(Press: 0.6 Torr)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  pyridin-2-yl(thiophen-3-yl)methanone 在 palladium on activated charcoal 氢气 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 55.0 ℃ 、137.9 kPa 条件下， 反应 72.0h， 生成 3-Pyridin-2-yl-3-thiophen-3-yl-propionic acid ethyl ester
  参考文献：
  名称：

  Imidazolines as efficacious glucose-dependent stimulators of insulin secretion

  摘要：

  Synthesis of a series of imidazolines with glucose dependent effects on insulin exocytosis from pancreatic P-cells is reported. Regioisomers and enantionters were found to exhibit marked differences in exocytotic effects as well as different activities on the K-ATP-channel- the (R (+)) isomer of 2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophene-2-ylethyl]pyridine (4a) and the (+) isomer of 2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophene-3-yiethyl]pyridine (4d) were found to give a significant increase in insulin release in contrast to Findings for their enantiomers-without influence on the K-ATP-channel. The (+) isomer (4a) showed glucose dependent insulin release from P-cells at concentrations above 2.5 mM and a marked glucose lowering effect in ob/ob mice as well as in fed but not in fasted rats. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00041-2
• 作为产物：
  描述：

  1-(2-pyridyl)-1-(3-thienyl)methane 在 氧气 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以73%的产率得到pyridin-2-yl(thiophen-3-yl)methanone
  参考文献：
  名称：

  简便合成杂环芳基酮类化合物的方法

  摘要：

  本发明公开了简便合成杂环芳基酮类化合物的方法，属于有机化学技术领域。以苄基杂环类化合物为反应原料，在极性溶剂中，氧气氛围下加热反应得到多取代的酮类化合物。本发明使用分子氧作为氧化剂，绿色、环保，直接促进Csp3‑H键的选择性氧化官能化来制备酮，拓宽了酮类化合物的合成方法。

  公开号：

  CN109134173B

文献信息

• [EN] LDHA ACTIVITY INHIBITORS<br/>[FR] INHIBITEURS D'ACTIVITÉ LDHA
  申请人：ARCTIC PHARMA AS

  公开号：WO2018211277A1

  公开（公告）日：2018-11-22

  The invention provides compounds of formula (I), stereoisomers, tautomers, pharmaceutically acceptable salts and prodrugs thereof: (I) wherein A1 to A6 and R1 to R4 are as defined herein. Such compounds are suitable for use in the treatment or prevention of diseases or conditions which are mediated by the activation of lactate dehydrogenase A (LDHA), for example cancer.

  该发明提供了式(I)的化合物，立体异构体，互变异构体，药学上可接受的盐及其前药：(I)其中A1至A6和R1至R4如本文所定义。这些化合物适用于治疗或预防由乳酸脱氢酶A(LDHA)激活介导的疾病或症状，例如癌症。
• Oral hypoglycaemic agents
  申请人：——

  公开号：US20020132812A1

  公开（公告）日：2002-09-19

  Compounds of formula (I) which are optionally substituted 2-(&ohgr;,&ohgr;-diarylalkyl)-4,5-dihydro-1H-imidazoles and 2-(&ohgr;,&ohgr;-diarylalkyl)-1,4,5,6-tetrahydropyrimidines and salts thereof with inorganic and organic acids have interesting pharmacological properties. Thus, the compounds are useful in the treatment of type 2 diabetes.

  式(I)的化合物，它们是可选择取代的2-(&ohgr;，&ohgr;-二芳基烷基)-4,5-二氢-1H-咪唑和2-(&ohgr;，&ohgr;-二芳基烷基)-1,4,5,6-四氢嘧啶及其与无机和有机酸的盐具有有趣的药理特性。因此，这些化合物在治疗2型糖尿病方面是有用的。
• Photoinduced Divergent Alkylation/Acylation of Pyridine <i>N</i>-Oxides with Alkynes under Anaerobic and Aerobic Conditions
  作者：Jin-hui Xu、Wen-bin Wu、Jie Wu

  DOI：10.1021/acs.orglett.9b01940

  日期：2019.7.5

  Ortho-alkylated and ortho-acylated pyridines have been conveniently synthesized from pyridine N-oxides and alkynes under visible-light-mediation in a metal-free manner. The alkynes served as both alkylating and acylating agents via switching between anaerobic and aerobic conditions. The overall strategy accommodates a broad scope of substituted pyridine N-oxides and alkynes, with excellent regioselectivity

  已经在可见光-介导下以无金属的方式方便地由吡啶N-氧化物和炔烃合成了邻烷基化和邻酰基化的吡啶。炔通过在厌氧和需氧条件之间切换而同时充当烷基化剂和酰化剂。总体策略适用于广泛范围的取代吡啶N-氧化物和炔烃，在许多情况下具有出色的区域选择性。
• Structure-based optimization of hydroxylactam as potent, cell-active inhibitors of lactate dehydrogenase
  作者：BinQing Wei、Kirk Robarge、Sharada S. Labadie、Jinhua Chen、Laura B. Corson、Antonio DiPasquale、Peter S. Dragovich、Charles Eigenbrot、Marie Evangelista、Benjamin P. Fauber、Anna Hitz、Rebecca Hong、Kwong Wah Lai、Wenfeng Liu、Shuguang Ma、Shiva Malek、Thomas O'Brien、Jodie Pang、David Peterson、Laurent Salphati、Deepak Sampath、Steven Sideris、Mark Ultsch、Zijin Xu、Ivana Yen、Dong Yu、Qin Yue、Aihe Zhou、Hans E. Purkey

  DOI：10.1016/j.bmcl.2022.128576

  日期：2022.3

  utilized to optimize 6,6-diaryl substituted dihydropyrone and hydroxylactam to obtain inhibitors of lactate dehydrogenase (LDH) with low nanomolar biochemical and single-digit micromolar cellular potencies. Surprisingly the replacement of a phenyl with a pyridyl moiety in the chemical structure revealed a new binding mode for the inhibitors with subtle conformational change of the LDHA active site.

  基于结构的设计用于优化 6,6-二芳基取代的二氢吡喃酮和羟基内酰胺，以获得具有低纳摩尔生化和个位数微摩尔细胞效力的乳酸脱氢酶 (LDH) 抑制剂。令人惊讶的是，在化学结构中用吡啶基部分取代苯基揭示了一种新的抑制剂结合模式，LDHA 活性位点的构象发生了细微的变化。这导致了一种有效的、具有细胞活性的羟内酰胺抑制剂的鉴定，该抑制剂具有适用于小鼠肿瘤异种移植研究的体内药代动力学特征。
• Asymmetric Hydroboration of Heteroaryl Ketones by Aluminum Catalysis
  作者：Yury Lebedev、Iuliia Polishchuk、Bholanath Maity、Miguel Dinis Veloso Guerreiro、Luigi Cavallo、Magnus Rueping

  DOI：10.1021/jacs.9b10364

  日期：2019.12.11

  of methyl aluminum complexes bearing chiral biphenol-type ligands were found to be highly active catalysts in the asymmetric reduction of heterocyclic ketones (S/C = 100 - 500, ee up to 99%). The protocol is suitable for a wide range of substrates and has a high tolerance to functional groups. The formed 2-heterocyclic-alcohols are valuable building blocks in drug discovery or can be used as ligands

  发现一系列带有手性双酚型配体的甲基铝配合物是杂环酮不对称还原的高活性催化剂（S/C = 100 - 500，ee 高达 99%）。该协议适用于广泛的底物，并且对官能团具有很高的耐受性。形成的 2-杂环醇是药物发现中的重要组成部分，或可用作不对称催化中的配体。反应中间体的分离和综合表征支持 DFT 计算提出的催化循环。