6-formyl-3-pyridinyl 4-methylbenzenesulfonate | 106984-95-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-formyl-3-pyridinyl 4-methylbenzenesulfonate
• 英文别名: (6-Formylpyridin-3-yl) 4-methylbenzenesulfonate
• CAS: 106984-95-6
• 化学式: C₁₃H₁₁NO₄S
• 分子量: 277.301
• InChiKey: HJMYTUAEMSAAGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-formyl-3-pyridinyl 4-methylbenzenesulfonate 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 1-<<5-<(p-tolylsulfonyl)oxy>-2-pyridyl>methyl>imidazole-2-thione hydrochloride
  参考文献：
  名称：

  Inhibitors of dopamine .beta.-hydroxylase. 3. Some 1-(pyridylmethyl)imidazole-2-thiones

  摘要：

  The 1-benzylimidazole-2-thione moiety has been previously shown by Kruse et al. to be broadly associated with dopamine beta-hydroxylase (DBH) inhibitory activity both in vitro and in vivo in spontaneously hypertensive rats (SHR). An extension of structure-activity studies to 1-(pyridylmethyl)- and 1-(oxypyridylmethyl)imidazole-2-thiones is reported here in an attempt to exploit the pH differential that exists across the chromaffin vesicle membrane. We hypothesized that the weakly basic pyridyl compounds would diffuse into the acidic vesicles in their neutral forms where protonation and concentration would occur to enhance their in vivo effectiveness as inhibitors. To test this hypothesis, isomeric 2-, 3- and 4-(1-pyridylmethyl)imidazole-2-thiones were synthesized from the appropriate pyridinecarboxaldehydes by reductive alkylation of aminoacetaldehyde dialkyl acetal followed by imidazole-2-thione formation using acidic potassium thiocyanate. Related oxypyridyl compounds were synthesized by first preparing the appropriate aldehyde intermediate followed by conversion to the imidazole-2-thione by the same procedure. The unsubstituted pyridylmethyl compounds showed modest DBH inhibition in vitro but, consistent with a transport-mediated increase in observed potency, showed significant effects in vivo to increase the vascular ratio of dopamine to norepinephrine and to lower blood pressure.

  DOI：

  10.1021/jm00391a008
• 作为产物：
  描述：

  3-羟基-6-甲基吡啶 在 manganese(IV) oxide 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 109.0h， 生成 6-formyl-3-pyridinyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Inhibitors of dopamine .beta.-hydroxylase. 3. Some 1-(pyridylmethyl)imidazole-2-thiones

  摘要：

  The 1-benzylimidazole-2-thione moiety has been previously shown by Kruse et al. to be broadly associated with dopamine beta-hydroxylase (DBH) inhibitory activity both in vitro and in vivo in spontaneously hypertensive rats (SHR). An extension of structure-activity studies to 1-(pyridylmethyl)- and 1-(oxypyridylmethyl)imidazole-2-thiones is reported here in an attempt to exploit the pH differential that exists across the chromaffin vesicle membrane. We hypothesized that the weakly basic pyridyl compounds would diffuse into the acidic vesicles in their neutral forms where protonation and concentration would occur to enhance their in vivo effectiveness as inhibitors. To test this hypothesis, isomeric 2-, 3- and 4-(1-pyridylmethyl)imidazole-2-thiones were synthesized from the appropriate pyridinecarboxaldehydes by reductive alkylation of aminoacetaldehyde dialkyl acetal followed by imidazole-2-thione formation using acidic potassium thiocyanate. Related oxypyridyl compounds were synthesized by first preparing the appropriate aldehyde intermediate followed by conversion to the imidazole-2-thione by the same procedure. The unsubstituted pyridylmethyl compounds showed modest DBH inhibition in vitro but, consistent with a transport-mediated increase in observed potency, showed significant effects in vivo to increase the vascular ratio of dopamine to norepinephrine and to lower blood pressure.

  DOI：

  10.1021/jm00391a008

文献信息

• 3-cyanoquinolines, 3-cyano-1,6-naphthyridines, and 3-cyano-1,7-naphthyridines as protein kinase inhibitors
  申请人：American Home Products Corporation

  公开号：US20020026052A1

  公开（公告）日：2002-02-28

  This invention provides compounds of Formula (I), having the structure 1 where T, Z, X, A, R 1 , R 2a , R 2b , R 2c , R 3 , R 4 , and n are defined herein, or a pharmaceutically acceptable salt thereof which are useful as antineoplastic agents and in the treatment of osteoporosis and polycystic kidney disease.

  这项发明提供了具有结构的化合物（I）的公式， 其中T、Z、X、A、R 1 、R 2a 、R 2b 、R 2c 、R 3 、R 4 和n在此处定义，或其药学上可接受的盐，这些化合物可用作抗肿瘤药物，并用于骨质疏松症和多囊肾病的治疗。
• Palladium-Catalyzed Arylation of (Di)azinyl Aldoxime Ethers by Aryl Iodides: Stereoselective Synthesis of Unsymmetrical (<i>E</i>)-(Di)azinylaryl Ketoxime Ethers
  作者：Quan Gou、Bin Deng、Jun Qin

  DOI：10.1002/chem.201501758

  日期：2015.9.1

  The first example of direct arylation of (di)azinyl aldoxime ethers by aryl iodides is reported. The reaction produces, in a single step, a variety of geometrically pure unsymmetrical (E)‐(di)azinylaryl ketoxime ethers, a class of nitrogenated motifs that have found wide applications in medicinal and organic chemistry but are difficult to access using conventional procedure. The utility of the method

  报道了由芳基碘化物直接使（二）氮烯基醛肟肟醚芳基化的第一个例子。该反应可在一个步骤中产生各种几何纯的不对称（E）-（二）氮杂芳基酮肟醚，这是一类氮化的基序，已在药物和有机化学中得到广泛应用，但使用常规方法很难获得。该方法的用途在默克黑色素浓缩激素1受体拮抗剂的正式合成中得到了进一步说明。
• [EN] 3-CYANOQUINOLINES,3-CYANO-1,6-NAPHTHYRIDINES, AND 3-CYANO-1,7-NAPHTHYRIDINES AS PROTEIN KINASE INHIBITORS<br/>[FR] 3-CYANOQUINOLINES,3-CYANO-1,6-NAPHTHYRIDINES ET 3-CYANO-1,7-NAPHTHYRIDINES UTILISEES COMME INHIBITEURS DE PROTEINEKINASE
  申请人：AMERICAN HOME PROD

  公开号：WO2001072711A1

  公开（公告）日：2001-10-04

  Compounds of Formula (I), having the structure or a pharmaceutically salt thereof are useful as antineoplastic agents and in the treatment of osteoporosis and polycystic kidney disease.

  具有结构式（I）或其药物盐的化合物在抗肿瘤药物和治疗骨质疏松症和多囊肾病方面是有用的。
• THIAZOLIDINE CARBOXAMIDE DERIVATIVES AS MODULATORS OF THE PROSTAGLANDIN F RECEPTOR
  申请人：PAGE Patrick Naxos

  公开号：US20080255094A1

  公开（公告）日：2008-10-16

  The present invention is related to thiazolidine carboxamide derivatives of formula (II) for the treatment and/or prophylaxis of preterm labor, premature birth, dysmenorrhea and for stopping labor prior to cesarean delivery.

  本发明涉及式（II）的噻唑烷羧酰胺衍生物，用于治疗和/或预防早产、早产、痛经以及在剖腹产前停止分娩。
• Dopamine-beta-hydroxylase inhibitors
  申请人：SMITHKLINE BECKMAN CORPORATION

  公开号：EP0214740A2

  公开（公告）日：1987-03-18

  Compounds of structure (I) in which Y is H, OH, halogen or C1-4 alkoxy; X is H, halogen, halo C1-4 alkyl, n is 1 to 5 and R is H or C1-4 alkyl and phar- maceu- tically acceptable salts or hydrates thereof, processes fortheir preparation, compositions containing them and their use in therapy.

  结构(I)的化合物 其中 Y 为 H、OH、卤素或 C1-4 烷氧基；X 为 H、卤素、卤代 C1-4 烷基，n 为 1 至 5，R 为 H 或 C1-4 烷基，以及它们的可接受盐或水合物。 及其可接受的盐或水合物、其制备工艺、含有它们的组合物以及它们在治疗中的用途。