6-(2-噻吩基)-2-吡啶醛 | 208111-00-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 6-(2-噻吩基)-2-吡啶醛
• 中文别名: 6-(噻吩-2-基)吡啶-2-甲醛
• 英文名称: 6-(2-thienyl)-2-pyridinecarboxaldehyde
• 英文别名: 6-(thiophen-2-yl)picolinaldehyde；6-(2-thienyl)-pyridine-2-carboxaldehyde；6-thiophen-2-ylpyridine-2-carbaldehyde
• CAS: 208111-00-6
• 化学式: C₁₀H₇NOS
• mdl: MFCD06410007
• 分子量: 189.238
• InChiKey: HZFJKPQZABOKLA-UHFFFAOYSA-N

物化性质

• 熔点：
  57-61 °C
• 沸点：
  324.7±32.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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

安全信息

• 危险品标志：
  Xn
• 海关编码：
  2934999090
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  6-(2-噻吩基)-2-吡啶醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 6-(噻吩-2-基)吡啶-2-甲醇
  参考文献：
  名称：

  吡啶衍生物与二氧化碳的氧化还原中性无金属三组分羰基化脱芳香化作用。

  摘要：

  吡啶-2-甲胺的TBD（1,3,5-三氮杂双环癸-5-烯）辅助的三组分羰基化是通过CO2作为良性CO替代物记录的。氧化还原中性方法能够以高收率（高达93％）和优异的化学选择性实现稠密官能化的咪唑并吡啶酮。组合的计算和实验研究表明，前所未有的RCOCl / TBD协同作用了二氧化碳的亲电活化。

  DOI：

  10.1002/chem.201904359
• 作为产物：
  描述：

  6-氯-2-羟甲基吡啶 在 镍 盐酸 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 四(三苯基膦)钯 、 Ti₂CO₃ 、 4 A molecular sieve 、 氢气 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 58.0h， 生成 6-(2-噻吩基)-2-吡啶醛
  参考文献：
  名称：

  Design and Synthesis of a Series of 6-Substituted-2-pyridinylmethylamine Derivatives as Novel, High-Affinity, Selective Agonists at 5-HT_1A Receptors

  摘要：

  A search for novel, selective agonists with high intrinsic activity at the 5-HT1A subtype of serotonin (5-HT) receptors was undertaken. Mechanistic and thermodynamic considerations led to the design of 6-substituted-2-pyridinylmethylamine as a potential 5-HT1A pharmacophore. Various adducts derived from the 6-substituted-2-pyridinylmethylamine moiety were tested for their affinity at 5-HT1A, alpha(1)-adrenergic, and D-2-dopaminergic receptors. Compounds with high affinity for 5-HT1A receptors (pK(i) greater than or equal to 8) were examined for agonist properties by measuring their ability to inhibit forskolin-stimulated cAMP production in HA7 cells (i.e., HeLa cells permanently transfected with the h5-HT1A receptor gene and expressing the h5-HT1A receptor protein). Several compounds of the type aryl{4-[(6-substituted-pyridin-2-ylmethylamino)methyl]piperidin-1-yl}methanone had nanomolar affinity for 5-HT1A binding sites and were more than 500-fold selective with respect to alpha(1) and D-2 sites. Importantly, their 5-HT1A agonist properties were demonstrated in HA7 cells where they behaved as potent inhibitors of cAMP accumulation. In particular, (3,4-dichlorophenyl){4-[(6-oxazol-5-ylpyridin-2-ylmethylamino)methyl]piperidin-1-yl}methanone (70) and (3,4-dichlorophenyl){4-[(6-azetidinopyridin-2-ylmethylamino)methyl]piperidin-1-yl}methanone (36) appeared to be more potent than, and at least as efficacious as, the prototypical 5-HT1A agonist (+/-)-8-OH-DPAT. SAR studies revealed that the pyridine nitrogen atom and the nature and the position of the substituents on the pyridine ring were critically involved in the ability of the compounds to recognize and activate 5-HT1A receptors. Structural modifications of the nonpharmacophoric part of the molecule showed, however, that the entire structure was required for affinity at 5-HT1A binding sites.

  DOI：

  10.1021/jm9804329

文献信息

• Aminopyrimidine Kinase Inhibitors
  申请人：Baldino Carmen M.

  公开号：US20110152235A1

  公开（公告）日：2011-06-23

  Disclosed are compounds, pharmaceutical compositions containing those compounds, and uses of the compounds and compositions as modulators of casein kinase 1 (e.g., CK1γ), casein kinase 2 (CK2), Pim 1, Pim2, Pim3, the TGFβ pathway, the Wnt pathway, the JAK/STAT pathway, and/or the mTOR pathway. Uses are also disclosed for the treatment or prevention of a range of therapeutic indications due at least in part to aberrant physiological activity of casein kinase 1 (e.g., CK1γ), casein kinase 2 (CK2), Pim 1, Pim2, Pim3, the TGFβ pathway, the Wnt pathway, the JAK/STAT pathway, and/or the mTOR pathway.

  揭示了化合物、含有这些化合物的药物组合物，以及这些化合物和组合物作为酪蛋白激酶1（例如CK1γ）、酪蛋白激酶2（CK2）、Pim 1、Pim2、Pim3、TGFβ途径、Wnt途径、JAK/STAT途径和/或mTOR途径调节剂的用途。还揭示了用于治疗或预防一系列治疗适应症的用途，至少部分原因是由于酪蛋白激酶1（例如CK1γ）、酪蛋白激酶2（CK2）、Pim 1、Pim2、Pim3、TGFβ途径、Wnt途径、JAK/STAT途径和/或mTOR途径的异常生理活性。
• Betti reaction enables efficient synthesis of 8-hydroxyquinoline inhibitors of 2-oxoglutarate oxygenases
  作者：C. C. Thinnes、A. Tumber、C. Yapp、G. Scozzafava、T. Yeh、M. C. Chan、T. A. Tran、K. Hsu、H. Tarhonskaya、L. J. Walport、S. E. Wilkins、E. D. Martinez、S. Müller、C. W. Pugh、P. J. Ratcliffe、P. E. Brennan、A. Kawamura、C. J. Schofield

  DOI：10.1039/c5cc06095h

  日期：——

  A Betti reaction was used for efficient generation of 2OG oxygenase inhibitors, including for KDM4 demethylases.

  使用Betti反应高效生成2OG氧化酶抑制剂，包括KDM4去甲基酶。
• [EN] IODONIUM ANALOGS AS INHIBITORS OF NADPH OXIDASES AND OTHER FLAVIN DEHYDROGENASES; FORMULATIONS THEREOF; AND USES THEREOF<br/>[FR] ANALOGUES D'IODONIUM EN TANT QU'INHIBITEURS DE NADPH OXYDASES ET D'AUTRES FLAVINES DÉSHYDROGÉNASES, LEURS FORMULATIONS ET LEURS UTILISATIONS
  申请人：US HEALTH

  公开号：WO2015157145A1

  公开（公告）日：2015-10-15

  Disclosed herein are novel iodonium analogs having anticancer and anti-inflammatory activity.

  本文披露了具有抗癌和抗炎活性的新型碘化物类似物。
• Dual-function Pd/NHC catalysis: tandem allylation–isomerization–conjugate addition that allows access to pyrroles, thiophenes and furans
  作者：Yaguang Bai、Shaohua Xiang、Min Li Leow、Xue-Wei Liu

  DOI：10.1039/c4cc01750a

  日期：——

  An efficient coupling reaction of allyl acetate with (O-azaaryl)carboxaldehyde by Pd–NHC dual catalysis has been developed. This reaction proceeds via direct coordination between the ortho nitrogen atom in the heterocycle and Pd(0). This dual catalysis is achieved under mild conditions to give 1,4-diones as products with up to 90% yield.

  通过 PdâNHC 双催化，开发出了乙酸烯丙酯与 (O-azaaryl)Carxaldehyde 的高效偶联反应。该反应通过杂环中的正交氮原子与钯（0）之间的直接配位进行。这种双催化反应是在温和的条件下进行的，产物为 1,4 二酮，收率高达 90%。
• A highly efficient dual catalysis approach for C-glycosylation: addition of (o-azaaryl)carboxaldehyde to glycals
  作者：Yaguang Bai、Wei Lin Leng、Yongxin Li、Xue-Wei Liu

  DOI：10.1039/c4cc06111j

  日期：——

  Dual catalysis by concurrent activation of glycals and (O-azaaryl)-carboxaldehydes using palladium and N-heterocyclic carbene has been developed. This activation through the formation of the Breslow intermediate and a π-allyl Pd complex is a novel and efficient approach to yield C-glycosides with yields up to 85%.

  通过同时激活甘露糖和（O-azaaryl）-羰基醛，使用钯和N-杂环卡宾进行双催化已经开发。通过形成Breslow中间体和π-烯丙基Pd配合物的激活是一种新颖高效的方法，可产生收率高达85%的C-糖苷。