6-羟基-2-(3-羟基苯基)-2,3-二氢色烯-4-酮 | 61429-74-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 6-羟基-2-(3-羟基苯基)-2,3-二氢色烯-4-酮
• 英文名称: 6-hydroxy-2-(3-hydroxyphenyl)chroman-4-one
• 英文别名: 6-Hydroxy-2-(3-hydroxy-phenyl)-chroman-4-on；6-hydroxy-2-(3-hydroxyphenyl)-2,3-dihydrochromen-4-one
• CAS: 61429-74-1
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: FTDCCBIDVVGONG-UHFFFAOYSA-N

物化性质

• 熔点：
  234-236 °C
• 沸点：
  529.5±50.0 °C(Predicted)
• 密度：
  1.386±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-羟基-2-(3-羟基苯基)-2,3-二氢色烯-4-酮 生成 4-[4,6-dihydroxy-2-(3-hydroxyphenyl)-2,3-dihydrochromen-4-yl]-2-(3-hydroxyphenyl)-2,3-dihydrochromene-4,6-diol
  参考文献：
  名称：

  SAHANA H. S.; TIWARI R. D., J. INDIAN CHEM. SOC. , 1976, 53, NO 5, 530-531

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-1-(2,5-dihydroxyphenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one 生成 6-羟基-2-(3-羟基苯基)-2,3-二氢色烯-4-酮
  参考文献：
  名称：

  SAHANA H. S.; TIWARI R. D., J. INDIAN CHEM. SOC. , 1976, 53, NO 5, 530-531

  摘要：

  DOI：

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。
• Comparing Drug Images and Repurposing Drugs with BioGPS and FLAPdock: The Thymidylate Synthase Case
  作者：Lydia Siragusa、Rosaria Luciani、Chiara Borsari、Stefania Ferrari、Maria Paola Costi、Gabriele Cruciani、Francesca Spyrakis

  DOI：10.1002/cmdc.201600121

  日期：2016.8.5

  Repurposing and repositioning drugs has become a frequently pursued and successful strategy in the current era, as new chemical entities are increasingly difficult to find and get approved. Herein we report an integrated BioGPS/FLAPdock pipeline for rapid and effective off-target identification and drug repurposing. Our method is based on the structural and chemical properties of protein binding sites

  随着新化学实体越来越难以找到和获得批准，重新定位和重新定位药物已成为当前时代的一种成功追求的成功策略。本文中，我们报告了一条集成的BioGPS / FLAPdock管道，可快速有效地进行脱靶识别和药物再利用。我们的方法基于蛋白质结合位点的结构和化学性质，即GRID分子相互作用域（MIF）中编码的配体图像。通过BioGPS算法，根据聚类的口袋测量口袋的重叠程度，可以揭示蛋白质的相似性。共结晶的和已知的配体可以在相似的靶标之间交叉对接，选择用于后续的体外结合实验，并且可能会提高抑制效力。我们使用人类胸苷酸合酶（TS）作为测试案例，并在整个RCSB蛋白质数据库（PDB）中搜索了类似的目标口袋。我们选择酪蛋白激酶IIalpha作为对照，并测试了其一系列针对TS模板的抑制剂。确定了鞣花酸和芹菜素为TS抑制剂，并在第二轮筛选中选择并合成了各种类黄酮。已证明这些化合物在低微摩尔范围内具有活性。
• Chroman-4-One Derivatives Targeting Pteridine Reductase 1 and Showing Anti-Parasitic Activity
  作者：Flavio Di Pisa、Giacomo Landi、Lucia Dello Iacono、Cecilia Pozzi、Chiara Borsari、Stefania Ferrari、Matteo Santucci、Nuno Santarem、Anabela Cordeiro-da-Silva、Carolina Moraes、Laura Alcantara、Vanessa Fontana、Lucio Freitas-Junior、Sheraz Gul、Maria Kuzikov、Birte Behrens、Ina Pöhner、Rebecca Wade、Maria Costi、Stefano Mangani

  DOI：10.3390/molecules22030426

  日期：——

  Flavonoids have previously been identified as antiparasitic agents and pteridine reductase 1 (PTR1) inhibitors. Herein, we focus our attention on the chroman-4-one scaffold. Three chroman-4-one analogues (1-3) of previously published chromen-4-one derivatives were synthesized and biologically evaluated against parasitic enzymes (Trypanosoma brucei PTR1-TbPTR1 and Leishmania major-LmPTR1) and parasites

  黄酮类化合物以前已被确定为抗寄生虫药和蝶啶还原酶1（PTR1）抑制剂。在本文中，我们将注意力集中在苯并吡喃-4-酮支架上。合成了先前发表的chromen-4-one衍生物的三个chroman-4-one类似物（1-3），并针对寄生酶（布鲁氏锥虫（Trypanosoma brucei）PTR1-TbPTR1和Leishmania major-LmPTR1）和寄生虫（Trypanosoma brucei和Leishmania infantum）进行了生物学评估。 。解析了与化合物1配合的TbPTR1的晶体结构和LmPTR1-黄酮配合物（化合物1和3）的第一晶体结构。通过比较所观察到的和预测的化合物结合模式来解释苯并吡喃-4-酮和苯并-4-酮衍生物的抑制活性。化合物1显示出针对目标酶和寄生虫的活性，选择性指数大于7且毒性低。我们的结果为进一步的支架优化和基于结构的药物设计提供了基础，该药物设计旨
• 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。