2-Oxo-3,4-dihydrochromene-3-carbonyl chloride | 161885-45-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: 2-Oxo-3,4-dihydrochromene-3-carbonyl chloride
• CAS: 161885-45-6
• 化学式: C₁₀H₇ClO₃
• 分子量: 210.617
• InChiKey: HXGWTMNPTQMUJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-氨丙基)吗啉 、 2-Oxo-3,4-dihydrochromene-3-carbonyl chloride 在 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 以81%的产率得到N-(3-morpholinopropyl)-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  New 2H-chromene-3-carboxamide derivatives: Design, synthesis and use as inhibitors of hMAO

  摘要：

  A series new 2H-chromene-3-carboxamide derivatives 4a-4t were synthesized and evaluated as monoamine oxidase A and B (MAO-A and MAO-B) inhibitors. Among them, compound 4d (IC50 = 0.93 μM, IC(50 iproniazid) = 7.80 μM) showed the most activity and higher MAO-B selectivity (64.5-fold vs. 1-fold) with respect to the MAO-A isoform. The active compound 4d was also docked into the hMAO-B complex structure active site to determine the probable binding model. The results indicated that conserved residue CYSA 172 was important for ligand binding via hydrogen bond interaction, Pi-Pi interaction was found between the benzene-ring of compound 4d and residue ILEA 199.

  DOI：

  10.1016/j.ejmech.2014.04.060
• 作为产物：
  描述：

  香豆素-3-羧酸乙酯 在 盐酸 、 氯化亚砜 、 sodium hydroxide 作用下， 反应 4.0h， 生成 2-Oxo-3,4-dihydrochromene-3-carbonyl chloride
  参考文献：
  名称：

  New 2H-chromene-3-carboxamide derivatives: Design, synthesis and use as inhibitors of hMAO

  摘要：

  A series new 2H-chromene-3-carboxamide derivatives 4a-4t were synthesized and evaluated as monoamine oxidase A and B (MAO-A and MAO-B) inhibitors. Among them, compound 4d (IC50 = 0.93 μM, IC(50 iproniazid) = 7.80 μM) showed the most activity and higher MAO-B selectivity (64.5-fold vs. 1-fold) with respect to the MAO-A isoform. The active compound 4d was also docked into the hMAO-B complex structure active site to determine the probable binding model. The results indicated that conserved residue CYSA 172 was important for ligand binding via hydrogen bond interaction, Pi-Pi interaction was found between the benzene-ring of compound 4d and residue ILEA 199.

  DOI：

  10.1016/j.ejmech.2014.04.060

文献信息

• ANTI-ARRHYTHMIC N-SUBSTITUTED 3-BENZAZEPINES OR ISOQUINOLINES
  申请人：SMITHKLINE BEECHAM LABORATOIRES PHARMACEUTIQUES

  公开号：EP0700389A1

  公开（公告）日：1996-03-13
• [EN] ANTI-ARRHYTHMIC N-SUBSTITUTED 3-BENZAZEPINES OR ISOQUINOLINES<br/>[FR] 3-BENZAZEPINES OU ISOQUINOLINES N-SUBSTITUEES A ACTION ANTIARYTHMIQUE
  申请人：SMITHKLINE BEECHAM LABORATOIRES PHARMACEUTIQUES

  公开号：WO1994027971A1

  公开（公告）日：1994-12-08

  (EN) A compound of formula (I) or a salt thereof, or a solvate thereof, wherein A represents CH2, (CH2)2, CO, COCH2, CH2CO, CSCH2 or CH=CH; B represents CH2 or CO; Z represents a bond, CH2, (CH2)2 or X-CH2-CH2 wherein X represents O or S; D represents CO, SO2, NH-CO, NH-SO2, CH=CH or P(O)OR6 wherein R6 is C1-6 alkyl; Q represents aryl, aralkyl, aralkenyl or aralkynyl, wherein the aryl moiety may be substituted or unsubstituted with 1 to 5 substituents selected from the list consisting of nitro, halogen, alkylsulfonamide, amino, 1-imidazo, alkyl or haloalkyl, or Q represents substituted or unsubstituted: furanyl, pyranyl, thienyl, thiazolyl, imidazolyl, triazolyl or the benzo fused equivalents of furanyl, pyranyl, thienyl, thiazolyl, imidazolyl or triazolyl, indolyl, oxoindolyl, indenyl, isoindenyl, indazolyl, indolizinyl or pyridinyl or cycloalkyl optionally fused to an aryl group; R1, R2, R3, R4 and R5 each independently represent H, alkyl, OH or alkoxy or, if attached to adjacent carbon atoms, any two of R1, R2, R3, R4 and R5 together with the carbon atoms to which they are attached may form a fused heterocyclic ring of four to six atoms wherein one, two or three of the said atoms are oxygen or nitrogen; and E represents C2-4 n-alkylene group wherein each carbon is optionally substituted by R6; a process for preparing such compounds, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine.(FR) Composé de la formule (I) ou sel ou solvant de ce composé. Dans cette formule, A représente CH2, (CH2)2, CO, COCH2, CH2CO, CSCH2 ou CH=CH; B représente CH2 ou CO; Z représente une liaison, CH2, (CH2)2 ou X-CH2-CH2 dans lequel X représente O ou S; D représente CO, SO2, NH-CO, NH-SO2, CH=CH ou P(O)OR6, R6 représentant alkyle C1-6; Q représente aryle, aralkyle, aralcényle ou aralkynyle, la fraction aryle étant substituée ou non par 1 à 5 substituants choisis dans la liste composée de nitro, halogène, alkylsulfonamide, amino, 1-imidazo, alkyle ou haloalkyle, ou Q représente furanyle, pyranyle, thiényle, thiazolyle, imidazolyle, triazolyle ou les équivalents benzo-fusionnés de furanyle, pyranyle, thiényle, thiazolyle, imidazolyle ou triazolyle, indolyle, oxoindolyle, indényle, isoindenyle, indazolyle, indolizinyle ou pyridinyle ou cycloalkyle éventuellement fusionné à un groupe aryle, tous substitués ou non substitués; R1, R2, R3, R4 et R5 représentent chacun indépendamment H, alkyle, OH, ou alcoxy ou, s'ils sont accolés à des atomes de carbone adjacents, deux éléments quelconques parmi R1, R2, R3, R4 et R5 forment, avec les atomes de carbone auxquels ils sont accolés, un noyau hétérocyclique fusionné de 4 à 6 atomes parmi lesquels un à trois sont des atomes d'oxygène ou d'azote; et E représente un groupe n-alkylène C2-4 dans lequel chaque atome de carbone est éventuellement substitué par R6. L'invention se rapporte également à un procédé de préparation de ces composés, à des compositions pharmaceutiques les comprenant, ainsi qu'à leur utilisation dans le domaine médical.
• New 2H-chromene-3-carboxamide derivatives: Design, synthesis and use as inhibitors of hMAO
  作者：Zhi-Xiang Pan、Xu He、Yan-Yan Chen、Wen-Jian Tang、Jing-Bo Shi、Yu-Lan Tang、Bao-An Song、Jun Li、Xin-Hua Liu

  DOI：10.1016/j.ejmech.2014.04.060

  日期：2014.6

  A series new 2H-chromene-3-carboxamide derivatives 4a-4t were synthesized and evaluated as monoamine oxidase A and B (MAO-A and MAO-B) inhibitors. Among them, compound 4d (IC50 = 0.93 μM, IC(50 iproniazid) = 7.80 μM) showed the most activity and higher MAO-B selectivity (64.5-fold vs. 1-fold) with respect to the MAO-A isoform. The active compound 4d was also docked into the hMAO-B complex structure active site to determine the probable binding model. The results indicated that conserved residue CYSA 172 was important for ligand binding via hydrogen bond interaction, Pi-Pi interaction was found between the benzene-ring of compound 4d and residue ILEA 199.