(E)-1-(3-bromo-5-chloro-2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(3-bromo-5-chloro-2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: 1-(3-bromo-5-chloro-2-hydroxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one；3'-Bromo-5'-chloro-2'-hydroxy-4-methoxychalcone
• 化学式: C₁₆H₁₂BrClO₃
• 分子量: 367.626
• InChiKey: HRQZDRHJMSZPNM-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (E)-1-(3-bromo-5-chloro-2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 在 盐酸 、 盐酸二甲胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 0.5h， 生成 8-Bromo-6-chloro-2-(4-methoxyphenyl)-3-methylidenechromen-4-one
  参考文献：
  名称：

  Synthesis of 3-Aminomethyl-2-aryl- 8-bromo-6-chlorochromones

  摘要：

  An efficient synthetic route to Cbz-protected 3-aminomethyl-2-aryl-8-bromo-6-chlorochromones has been developed. 3-Aryl-1-(3-bromo-5-chloro-2-hydroxyphenyl)-2-propen-1-one or 2-aryl-8-bromo-6-chlorochroman-4-one could be reacted under Mannich conditions yielding 2-aryl-8-bromo-6-chloro-3-methylenechroman-4-one, which was further converted to the target compound via an aza-Michael reaction followed by an SeO2 oxidation. This procedure represents a new method to introduce a primary aminomethyl group at the 3-position of a 2-arylchromone scaffold. The Cbz-protected 3-aminomethyl-2-aryl-8-bromo-6-chlorochromones can, e.g., be used in the synthesis of chromone-based beta-turn peptidomimetics.

  DOI：

  10.1021/ol062478z
• 作为产物：
  描述：

  3'-溴-5'-氯-2'-羟基苯乙酮 、 4-甲氧基苯甲醛 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以90%的产率得到(E)-1-(3-bromo-5-chloro-2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  微管蛋白聚合的抑制剂和促进剂：查耳酮和相关二烯酮作为潜在抗癌剂的合成和生物学评估

  摘要：

  合成了一系列二卤代查耳酮和与结构相关的二烯酮，并评估了它们在10种不同癌细胞系中的抗增殖活性以及它们对微管组装的影响。所有化合物均显示出细胞毒活性，IC 50值在5–280μM范围内，这取决于查耳酮的结构和细胞系。发现其中五种化合物是微管蛋白聚合抑制剂。相反，发现其中一种化合物能将微管蛋白稳定到与抗癌药多西他赛相同的程度。分子模型表明，微管蛋白抑制剂与β-微管蛋白的秋水仙碱结合位点结合，而新型微管蛋白稳定剂似乎与紫杉醇结合位点相互作用。

  DOI：

  10.1016/j.bmc.2011.03.005

文献信息

• Synthesis of Isomeric Δ²-Pyrazolines From 2′-Hydroxy-5′-chlorochalcones and its Derivatives
  作者：M. M. Ali、A. G. Doshi、P. B. Raghuwanshi

  DOI：10.1080/00397910008086963

  日期：2000.9

  Abstract Suitably substituted 2′-hydroxy-5′-chlorochalcones with hydrazine hydrochloride in refluxing DMF afforded isomeric Δ2-pyrazolines, which were characterized on the basis of chemical and spectral data.

  摘要 在回流的 DMF 中用盐酸肼适当取代 2'-羟基-5'-氯查耳酮得到异构体 Δ2-吡唑啉，并根据化学和光谱数据对其进行表征。
• Synthesis of 2,3,6,8-Tetrasubstituted Chromone Scaffolds
  作者：Kristian Dahlén、Erik A. A. Wallén、Morten Grøtli、Kristina Luthman

  DOI：10.1021/jo061008f

  日期：2006.9.1

  A useful and efficient synthetic strategy to 2,3,6,8-tetrasubstituted chromone derivatives has been developed. 2-Aryl/styryl-8-bromo-6-chloro-3-hydroxychromone derivatives were synthesized and used as scaffolds by introducing a variety of substituents in the 3-, 6-, and 8-positions using palladium-mediated reactions. Excellent regioselectivity in all positions could be obtained by performing reactions in the 8-position first, in which Stille, Heck, Suzuki, and Sonogashira reactions gave good to excellent yields of product (63-98%). Stille and Heck reactions in the 6- position also gave the desired products in good yields (64-86%). The hydroxy group in the 3- position was activated as a triflate and used in productive Stille reactions (63-94%). This hydroxyl group was also used in O-alkylation reactions with different functionalized alkyl bromides (57-88%). The flavonoids, which are based on the chromone structure, and other related ring systems, have several interesting biological activities. The chromones are also interesting structural scaffolds, and they have for example been designed to be used as mimetics of short peptides. The versatile applicability of chromone derivatives and especially their potential use in drug discovery implicates the importance of access to efficient synthetic routes to such compounds.
• Compounds exhibiting efflux inhibitor activity and composition and uses thereof
  申请人：Wempe Fitzpatrick Michael

  公开号：US20070254859A1

  公开（公告）日：2007-11-01

  At least one compound chosen from compounds of Formula I: a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a prodrug thereof, and mixtures of any of the foregoing, wherein: n is a number from 1 to 900, wherein the individual units may be the same or different; W is chosen from alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; each of R 2 , R 3 , R 4 and R 5 is independently chosen from —H, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; Z′ is chosen from —O—, —N—, —NO—, —NR 4 —, —S—, —SO— and —SO 2 —, wherein R 4 is defined as above; each of X, X′, Y and Z is independently chosen from —CR 4 R 5 —, —NH—, —NR 4 —, —NO—, —O—, —NOR 4 —, —S—, —SO—, —SO 2 —, wherein R 4 and R 5 are defined as above; R 1 is chosen from a tocopherol, a steroid and a flavonoid; and R 6 is chosen from any R 1 , alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl.
• ESTROGEN RECEPTOR ALPHA COLIGANDS, AND METHODS OF USE THEREOF
  申请人：The Regents of the University of California

  公开号：US20190008797A1

  公开（公告）日：2019-01-10

  Provided herein is a coligand for the estrogen receptor (ER) a subunit, and methods of use thereof in treating conditions associated with ER signaling in an individual. The present ERα coligand may be a cell type-selective, allosteric modulator of ERα signaling. The ERα coligand, when administered to an individual, may modulate ER agonist-dependent signaling in a tissue-selective manner.
• [EN] COMPOUNDS EXHIBITING EFFLUX INHIBITOR ACTIVITY AND COMPOSITIONS AND USES THEREOF<br/>[FR] COMPOSES PRESENTANT UNE ACTIVITE INHIBITRICE DE L'ECOULEMENT, COMPOSITIONS ET UTILISATIONS DE CEUX-CI
  申请人：EASTMAN CHEM CO

  公开号：WO2007115181A9

  公开（公告）日：2008-04-03

  [EN] At least one compound chosen from compounds of Formula 1: a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a prodrug thereof, and mixtures of any of the foregoing, wherein: n is a number from 1 to 900, wherein the individual units may be the same or different; W is chosen from alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; each Of R₂, R₃, R₄ and R₅ is independently chosen from -H, alkyl, substituted aikyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl; Z' is chosen from -O-, -N-, -NO-, - NR₄-, -S-, -SO- and -SO₂-, wherein R₄ is defined as above; each of X, X', Y and Z is independently chosen from -CR₄R₅-, -NH-, -NR₄-, -NO-. -O-, -NOR₄-, -S-, -SO-, -SO₂-, wherein R₄ and R₅ are defined as above; R₁ is chosen from a tocopherol, a steroid and a flavonoid; and R₆, is chosen from any R₁, alkyl. substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, substituted aryl, aralkyl and substituted aralkyl.
  [FR] La présente invention concerne au moins un composé choisi parmi les composés de formule 1 : un sel ou un ester pharmaceutiquement acceptable de celui-ci, un solvate de celui-ci, un chélate de celui-ci, un complexe non covalent de celui-ci, un promédicament de celui-ci et des mélanges de ces derniers, n étant un nombre de 1 à 900, les unités individuelles pouvant être identiques ou différentes, W étant choisi parmi l'alkyle, l'alkyle substitué, le cycloalkyle, le cycloalkyle substitué, l'aryle, l'aryle substitué, l'aralkyle et l'aralkyle substitué, R₂, R₃, R₄ et R₅ étant chacun indépendamment choisi parmi -H, alkyle, alkyle substitué, cycloalkyle, cycloalkyle substitué, aryle, aryle substitué, aralkyle et aralkyle substitué, Z' étant choisi parmi -O-, -N-, -NO-, - NR₄-, -S-, -SO- et -SO₂-, R₄ étant tel que défini ci-dessus, X, X', Y et Z étant chacun indépendamment choisi parmi -CR₄R₅-, -NH-, -NR₄-, -NO-, -O-, -NOR₄-, -S-, -SO-, -SO₂-, R₄ et R₅ étant tels que définis ci-dessus, R₁ étant choisi parmi un tocophérol, un stéroïde et un anthoxanthine, et R₆ étant choisi parmi R₁, alkyle, alkyle substitué, cycloalkyle, cycloalkyle substitué, aryle, aryle substitué, aralkyle et aralkyle substitué.