6-(1,3-dioxolan-2-yl)picolinaldehyde | 154955-94-9

• 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
• 英文名称: 6-(1,3-dioxolan-2-yl)picolinaldehyde
• 英文别名: 6-[1,3]Dioxolan-2-yl-pyridine-2-carbaldehyde；6-(1,3-dioxolan-2-yl)pyridine-2-carbaldehyde
• CAS: 154955-94-9
• 化学式: C₉H₉NO₃
• 分子量: 179.175
• InChiKey: LJIDTODXBHZDEV-UHFFFAOYSA-N

物化性质

• 沸点：
  310.5±42.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(1,3-dioxolan-2-yl)picolinaldehyde 在 甲酸 、 potassium carbonate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 6.0h， 生成 [1-(6-Oxazol-5-yl-pyridin-2-yl)-meth-(E)-ylidene]-piperidin-4-ylmethyl-amine
  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
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 2-溴-6-(1,3-二氧戊环-2-基)吡啶 在 正丁基锂 作用下， 以20%的产率得到6-(1,3-dioxolan-2-yl)picolinaldehyde
  参考文献：
  名称：

  On the chemistry of pyrrole pigments, XC: Pyridinologous linear tri- and tetrapyrroles

  摘要：

  One pyridinologous linear tripyrrole and two pyridinologous linear tetrapyrroles were prepared, and their structural aspects derived from spectroscopic measurements and force field calculations. The properties of these novel pyrrole pigments are compared with those of analogous linear tri- and tetrapyrroles.

  DOI：

  10.1007/bf00816411

文献信息

• [EN] SUBSTITUTED TRICYCLIC AMIDES, ANALOGUES THEREOF, AND METHODS USING SAME<br/>[FR] AMIDES TRICYCLIQUES SUBSTITUÉS, ANALOGUES DE CEUX-CI ET PROCÉDÉS LES METTANT EN OEUVRE
  申请人：ARBUTUS BIOPHARMA CORP

  公开号：WO2021229302A1

  公开（公告）日：2021-11-18

  The present disclosure includes substituted tricyclic amides, or analogues thereof of formula (I) (I), wherein X, Y, ring A, R1, R5, R6 and R7 are as defined herein, and compositions comprising compounds of formula (I) that can be used to treat or prevent hepatitis B virus (HBV) and/or hepatitis D virus (HDV) infections in a patient.

  本公开涵盖了替代三环酰胺，或其类似物的化合物，其化学式为(I)，其中X、Y、环A、R1、R5、R6和R7如本文所定义，并包括化合物(I)的组合物，可用于治疗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。
• [EN] DIACYLGLYCEROL ACYLTRANSFERASE 2 INHIBITORS<br/>[FR] INHIBITEURS DE DIACYLGLYCÉROL ACYLTRANSFÉRASE 2
  申请人：PFIZER

  公开号：WO2013150416A1

  公开（公告）日：2013-10-10

  Derivatives of purine, 3H-imidazo[4,5-b]pyrimidine and 1H- imidazo[4,5-d]pyrazine of Formula I that inhibit the activity of the diacylglycerol acyltransferase 2 (DGAT2) and their uses in the treatment of diseases linked thereto in animals are described herein.

  这里描述了抑制二酰基甘油酰基转移酶2（DGAT2）活性的嘌呤衍生物，即式I的3H-咪唑并[4,5-b]嘧啶和1H-咪唑并[4,5-d]吡嗪，以及它们在治疗相关动物疾病中的用途。
• Pyridin-2-yl-methylamine derivatives, method of preparing and
  申请人：Pierre Fabre Medicament

  公开号：US06020345A1

  公开（公告）日：2000-02-01

  The invention concerns novel pyridin-2-yl-methylamine derivatives of formula (I): ##STR1## in which: u represents hydrogen or methyl; v represents hydrogen, chlorine, or methyl; w represents hydrogen, fluorine, or methyl; x represents hydrogen or fluorine; y represents chlorine or methyl; z represents hydrogen, fluorine, chlorine, or methyl; A represents hydrogen, fluorine, chlorine, C.sub.1 -C.sub.5 alkyl, fluoroalkyl, cyclopropyl, a 5-membered aromatic heterocyclic group, alkoxy or alkythio, amino, cyclic amino, or alkoxycarbonyl. These compounds are useful as medicines, in particular as antidepressants or analgesics.

  本发明涉及一种新颖的吡啶-2-基甲胺衍生物，其通式为(I)：##STR1## 其中：u代表氢或甲基；v代表氢、氯或甲基；w代表氢、氟或甲基；x代表氢或氟；y代表氯或甲基；z代表氢、氟、氯或甲基；A代表氢、氟、氯、C1-C5烷基、氟代烷基、环丙基、5元芳香杂环基团、烷氧基、硫代烷基、氨基、环状氨基或烷氧羰基。这些化合物可作为药物使用，特别是作为抗抑郁药或镇痛药。
• Electronic structural dependence of the photophysical properties of fluorescent heteroditopic ligands – implications in designing molecular fluorescent indicators
  作者：Ali H. Younes、Lu Zhang、Ronald J. Clark、Michael W. Davidson、Lei Zhu

  DOI：10.1039/c0ob00482k

  日期：——

  Two fluorescent heteroditopic ligands (2a and 2b) for zinc ion were synthesized and studied. The efficiencies of two photophysical processes, intramolecular charge transfer (ICT) and photoinduced electron transfer (PET), determine the magnitudes of emission bathochromic shift and enhancement, respectively, when a heteroditopic ligand forms mono- or dizinc complexes. The electron-rich 2b is characterized

  合成并研究了锌离子的两种荧光异双位配体（2a和2b）。当异双位配体形成单或二锌复合体。富电子2b的特点是在激发态具有高度的 ICT，对 PET 的倾向很小，这表现为发射的大红移锌2+配位而不增加荧光量子产率。缺乏电子的2a显示出相反的光物理结果，其中锌2+结合导致发射大大增强而没有显着的光谱偏移。电子结构对2a和2b中 ICT 和 PET 相对效率的影响以及锌2+- 使用实验和计算方法探测协调。这项研究表明，在异源配体中设计的各种光物理途径（例如ICT 和 PET）之间的微妙平衡敏感地依赖于配体的电子结构，即荧光团是富电子还是贫电子，它是否拥有供体——受体类型的结构，以及发生金属结合的位置。
• [EN] PYRIDIN-2-YL-METHYLAMINE DERIVATIVES, METHOD OF PREPARING AND APPLICATION AS MEDICINE<br/>[FR] DERIVES DE LA PYRIDIN-2-YL-METHYLAMINE, LEUR PROCEDE DE PREPARATION ET LEUR APPLICATION COMME MEDICAMENTS
  申请人：PIERRE FABRE MEDICAMENT

  公开号：WO1998022459A1

  公开（公告）日：1998-05-28

  (EN) The invention concerns novel pyridin-2-yl-methylamine derivatives of formula (I) in which: u represents a hydrogen atom or a methyl radical; v represents a hydrogen atom or a chlorine atom or a methyl radical; w represents a hydrogen atom or a fluorine atom or a methyl radical; x represents a hydrogen atom or a fluorine atom; y represents a chlorine atom or a methyl radical; z represents a hydrogen atom or a fluorine atom or a chlorine atom or a methyl radical; A represents a hydrogen atom or a fluorine atom or a chlorine atom; a C1-C5 alkyl radical; a fluoroalkyl radical; a cyclopropyl radical; an aromatic heterocyclic group with 5 chains; an alkoxy or alkythio group; an amine group; an amino cyclic group; an alkoxycarbonyl group. These compounds are useful as medicine in particular as antidepressant or analgesic.(FR) La présente invention concerne de nouveaux dérivés de la pyridin-2-yl-méthylamine de formule (I) dans laquelle: u représente un atome d'hydrogène ou un radical méthyl; v représente un atome d'hydrogène ou un atome de chlore ou un radical méthyl; w représente un atome d'hydrogène ou un atome de fluor ou un radical méthyl; x représente un atome d'hydrogène ou un atome de fluor; y représente un atome de chlore ou un radical méthyl; z représente un atome d'hydrogène ou un atome de fluor ou un atome de chlore ou un radical méthyl; A représente: un atome d'hydrogène ou un atome de fluor ou un atome de chlore; un radical alkyl en C1-C5; un radical fluoroalkyl; un radical cyclopropyl; un groupe hétérocyclique aromatique à 5 chaînons; un groupe alkoxy ou alkylthio; un groupe amino; un groupe amino cyclique; un groupe alkoxycarbonyl. Ces composés sont utiles comme médicaments notamment comme antidépresseurs et analgésiques.

  该发明涉及公式（I）的新型吡啶-2-基甲胺衍生物：其中，u代表氢原子或甲基基团；v代表氢原子或氯原子或甲基基团；w代表氢原子或氟原子或甲基基团；x代表氢原子或氟原子；y代表氯原子或甲基基团；z代表氢原子或氟原子或氯原子或甲基基团；A代表氢原子或氟原子或氯原子；C1-C5烷基基团；氟烷基基团；环丙基基团；带有5个链的芳香杂环基团；烷氧基或烷硫基团；胺基团；氨基环基团；烷氧羰基团。这些化合物在医学上有用，特别是作为抗抑郁剂或镇痛剂。