2-(2-chlorophenyl)-6-hydroxychroman-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(2-chlorophenyl)-6-hydroxychroman-4-one
• 英文别名: 2-(2-chlorophenyl)-6-hydroxy-2,3-dihydrochromen-4-one
• 化学式: C₁₅H₁₁ClO₃
• 分子量: 274.704
• InChiKey: DLKBBAAQEGHPKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Phenylchroman-4,6-diol 、 2-(2-chlorophenyl)-6-hydroxychroman-4-one 生成 2-(2-chlorophenyl)chroman-4,6-diol
  参考文献：
  名称：

  Compounds, which are potent inhibitors of Na+ /Ca2+ exchange mechanism and are useful in the treatment of arrhythmias

  摘要：

  式(I)中所示的治疗活性化合物：其中在式(I)中所示的变量在本文中有定义；以及其药学上可接受的盐和酯。这些化合物是钠/钙交换机制的强效抑制剂。

  公开号：

  US07425568B2
• 作为产物：
  描述：

  2-氯苯甲醛 、 2,5-二羟基苯乙酮 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 48.0h， 以18%的产率得到(E)-3-(2-chlorophenyl)-1-(2,5-dihydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, antioxidant, in silico and computational investigation of 2,5-dihydroxyacetophenone derived chloro-substituted hydroxychalcones, hydroxyflavanones and hydroxyflavindogenides

  摘要：

  An imbalance between reactive oxygen species (ROS) and their elimination by antioxidants damages the cell and infect whole organism. The biological defence system against oxidative stress injury is Kelch-like ECH associated protein 1 (Keap1)-nuclear factor erythroid 2-related factor 2 (Nrf2)-antioxidant response elements (ARE) pathways. Antioxidants activate the Nrf2-ARE-Keap1 pathway and suppress the oxidative stress. Flavonoids are well known medicinal compounds inheriting antioxidant efficacy and wide spectrum of pharmacological activities. The study is aimed to synthesise, characterize and evaluate pharmacological activities of synthesized chloro-derivatives of flavonoids. Chloro-derivatives of flavonoids were synthesized and characterized by IR, 1H NMR and 13C NMR. Antioxidant potential of each synthesized compound was evaluated and then subjected to molecular docking with Keap1 (PDB ID: 2FLU) for the activation of Nrf2 and computational studies were performed by using DFT approach. Among the synthesized compounds compound 1a exhibited lower IC50 value. While docking and computational studies infer that compound 3c is a good Nrf2 activator and radical scavenger with highest docking score and lower energy gaps and IP values compared to references. Hence, it might be considered for further molecular studies for the treatment of inflammatory diseases through Nrf2-ARE-Keap1 pathway.Communicated by Ramaswamy H. Sarma.HighlightsChloro-substituted hydroxychalcones, hydroxyflavanones and hydroxyflavindogenides were synthesized.Antioxidant potential was accessed, compound 1a exhibited good antioxidant potential.In silico study was performed with Keap1, compound 3c have shown highest docking score with Keap1.DFT approach was used to explore the structure activity relationship.

  DOI：

  10.1080/07391102.2021.1943527

文献信息

• [EN] PYRIDINE DERIVATIVES USEFUL FOR INHIBITING SODIUM/CALCIUM EXCHANGE SYSTEM<br/>[FR] DERIVES PYRIDINE SERVANT A INHIBER LE SYSTEME D'ECHANGE SODIUM/CALCIUM
  申请人：ORION CORP

  公开号：WO2004063191A1

  公开（公告）日：2004-07-29

  Therapeutically active compounds of formula (I) or (II) wherein X is -O-, -CH2- or -C(O)-; Z is -CHR12- or a valence bond; Y is -CH2-, -C(O)-, CH(OR13)-, -O-, -S-; provided that in case Z is a valence bond, Y is not C(O); the dashed line representing an optional double bond in which case Z is -CR12- ­and Y is -CH2-, -C(O)- or -CH(OR10)- (in formula II) or -CH- (in formula I); R2 and R3 are independently H, lower alkyl, lower alkoxy, -NO2, halogen, -CF3, -OH, benzyloxy or a group of formula (IIIa). R1 is H, CN, halogen, -CONH2, -COOR15, CH2NR15R18, NHC(O)R5, NHCH2R5, NHR20, NR21R22, NHC(NH)NHCH3 or, in case the compound is of formula (II) wherein the optional double bond exists or in case R2 or R3 is benzyloxy or a group of formula (IIIa) or in case the pyridine ring of formula (I) or (II) is attached to the oxygen atom in 3-, 4- or 5-position, R1 can also be -NO2 or NR16R17; R4 is H, -NO2, CN, halogen, -CONH2, -COOR15, -CH2NR15R18, -NR16R17, NHC(O)R5 or -NHC(NH)NHCH3; R5 is alkyl substituted with 1-3 substituents selected from the group consisting of halogen, amino and hydroxy, or carboxyalkyl, in which the alkyl portion is optionally substituted with 1-3 substituents selected from the group consisting of halogen, amino and hydroxyl, -CHR6NR,R8 or one of the following groups: formula (IVa), (IVb), (IVc), (IVd), (IVe), and pharmaceutically acceptable salts and esters thereof. The compounds are potent inhibitors of Na+/Ca2+ exchange mechanism.

  式（I）或（II）的治疗活性化合物，其中X为-O-，-CH2-或-C（O）-；Z为-CHR12-或一个价键；Y为-CH2-，-C（O）-，CH（OR13）-，-O-，-S-；条件是如果Z为一个价键，则Y不是C（O）；虚线表示可选的双键，此时Z为-CR12-，Y为-CH2-，-C（O）-或-CH（OR10）-（在式（II）中）或-CH-（在式（I）中）；R2和R3独立地为H，较低的烷基，较低的烷氧基，-NO2，卤素，-CF3，-OH，苄氧基或式（IIIa）的基团。R1为H，CN，卤素，-CONH2，-COOR15，CH2NR15R18，NHC（O）R5，NHCH2R5，NHR20，NR21R22，NHC（NH）NHCH3的基团，或者，如果化合物为式（II），其中存在可选的双键，或者如果R2或R3为苄氧基或式（IIIa）的基团，或者如果式（I）或（II）的吡啶环附着在3-，4-或5-位置的氧原子上，则R1也可以是-NO2或NR16R17；R4为H，-NO2，CN，卤素，-CONH2，-COOR15，-CH2NR15R18，-NR16R17，NHC（O）R5或-NHC（NH）NHCH3；R5为烷基，其上取代有1-3个取自卤素、氨基和羟基或羧基的取代基，其中烷基部分可选地取代有1-3个取自卤素、氨基和羟基的取代基，-CHR6NR,R8或以下所示的一个基团之一：式（IVa），（IVb），（IVc），（IVd），（IVe），以及其药用可接受的盐和酯。这些化合物是Na+/Ca2+交换机制的有效抑制剂。
• Compounds, which are potent inhibitors of na+ / ca2+ exchange mechanism and are useful in the treatment of arrhythmias
  申请人：——

  公开号：US20040235905A1

  公开（公告）日：2004-11-25

  Therapeutically active compounds of formula (I): wherein X is —O—, —CH 2 — or —C(O)—; Z is —CHR 9 — or valence bond; Y is —CH 2 —, —C(O)—, CH(OR 10 )—, —CH(NR 11 R 12 )—, —O—, —S—, —S(O)— or —S(O 2 )—, provided that in case Z is a valence bond, Y is not C(O); the dashed line represents an optional double bond in which case Z is —CR 9 — and Y is —CH—, C(OR 10 )— or —C(NR 11 R 12 )—; R 1 is —(CH 2 ) n NR 4 R 7 or one of the following groups: n is 1-4; R 2 and R 3 are independently H, lower alkyl, lower alkoxy, —NO 2 , halogen, —CF 3 , —OH, —NHR 8 or —COOH, R 4 and R 7 are independently H, lower alkyl or lower hydroxyalkyl; R 5 is H, lower alkoxy, —CF 3 , —NH 2 or —CN; R 6 is —NO 2 , —NR 14 R 19 , —CF 3 or R 8 and R 16 are independently H or acyl; R 9 is H or lower alkyl; R 10 is H, alkylsulfonyl or acyl; R 11 and R 12 are independently H, lower alkyl or acyl; R 13 and R 18 are independently H or —OR 20 ; R 14 and R 19 are independently H, acyl, alkylsulfonyl, C(S)NHR 17 or C(O)NHR 17 ; R 15 is H or NH 2 ; R 17 is H or lower alkyl; R 20 is H or acyl; and pharmaceutically acceptable salts and esters thereof are disclosed. The compounds are potent inhibitors of Na + /Ca 2+ exchange mechanism. 1

  公式（I）中的治疗活性化合物：其中X是—O—，—CH2—或—C（O）—; Z是—CHR9—或价键; Y是—CH2—，—C（O）—，CH（OR10）—，—CH（NR11R12）—，—O—，—S—，—S（O）—或—S（O2）—，前提是如果Z是价键，则Y不是C（O）; 虚线表示可选的双键，在这种情况下Z是—CR9—，Y是—CH—，C（OR10）—或—C（NR11R12）—; R1是—（CH2）nNR4R7或以下组之一：n为1-4; R2和R3独立地为H，较低的烷基，较低的烷氧基，—NO2，卤素，—CF3，—OH，—NHR8或—COOH，R4和R7独立地为H，较低的烷基或较低的羟基烷基; R5为H，较低的烷氧基，—CF3，—NH2或—CN; R6为—NO2，—NR14R19，—CF3或R8和R16独立地为H或酰基; R9为H或较低的烷基; R10为H，烷基磺酰基或酰基; R11和R12独立地为H，较低的烷基或酰基; R13和R18独立地为H或—OR20; R14和R19独立地为H，酰基，烷基磺酰基，C（S）NHR17或C（O）NHR17; R15为H或NH2; R17为H或较低的烷基; R20为H或酰基; 其药学上可接受的盐和酯被披露。这些化合物是钠/钙交换机制的有效抑制剂。
• Pyridine derivatives useful for inhibiting sodium/calcium exchange system
  申请人：Otsomaa Leena

  公开号：US20060241147A1

  公开（公告）日：2006-10-26

  Therapeutically active compounds of formula (I) or (II): wherein the variables in formulas (I) and (II) are defined in the description, and pharmaceutically acceptable salts and esters thereof. The compounds are potent inhibitors of Na + /Ca 2+ exchange mechanism.

  公式（I）或（II）的治疗活性化合物： 其中公式（I）和（II）中的变量在说明中定义，并且其药学上可接受的盐和酯。这些化合物是钠/钙交换机制的有效抑制剂。
• COMPOUNDS, WHICH ARE POTENT INHIBITORS OF NA+/CA2+ EXCHANGE MECHANISM AND ARE USEFUL IN THE TREATMENT OF ARRHYTHMIAS
  申请人：Orion Corporation

  公开号：EP1412343B1

  公开（公告）日：2006-08-30
• NEW COMPOUNDS, WHICH ARE POTENT INHIBITORS OF NA+/CA2+ EXCHANGE MECHANISM AND ARE USEFUL IN THE TREATMENT OF ARRHYTHMIAS
  申请人：ORION CORPORATION

  公开号：EP1412343A1

  公开（公告）日：2004-04-28