3-(5-bromo-2-hydroxyphenyl)-1-(4-bromophenyl)prop-2-en-1-one | 93513-95-2

• 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: 3-(5-bromo-2-hydroxyphenyl)-1-(4-bromophenyl)prop-2-en-1-one
• 英文别名: 1-(4-Bromphenyl)-3-(5-brom-2-hydroxyphenyl)-propen-(2)-on-(1)
• CAS: 93513-95-2
• 化学式: C₁₅H₁₀Br₂O₂
• 分子量: 382.051
• InChiKey: IXRDXAMXXWCEJN-UHFFFAOYSA-N

物化性质

• 熔点：
  178-178.5 °C
• 沸点：
  491.1±45.0 °C(Predicted)
• 密度：
  1.731±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(5-bromo-2-hydroxyphenyl)-1-(4-bromophenyl)prop-2-en-1-one 在 一水合肼 作用下， 反应 8.0h， 生成
  参考文献：
  名称：

  Synthesis, biological evaluation of novel 4,5-dihydro-2H-pyrazole 2-hydroxyphenyl derivatives as BRAF inhibitors

  摘要：

  A series of novel 4,5-dihydropyrazole derivatives (3a-3t) containing hydroxyphenyl moiety as potential V600E mutant BRAF kinase (BRAF(V600E)) inhibitors were designed and synthesized. Docking simulation was performed to insert compounds 3d (1-(5-(5-chloro-2-hydroxyphenyl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone) and 3m (1-(3-(4-chlorophenyl)-5-(3,5-dibromo-2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone) into the crystal structure of BRAF(V600E) to determine the probable binding model, respectively. Based on the preliminary results, compound 3d and 3m with potent inhibitory activity in tumor growth may be a potential anticancer agent. Results of the bioassays against BRAF(V600E), MCF-7 human breast cancer cell line and WM266.4 human melanoma cell line all showed several compounds had potent activities IC50 value in low micromolar range, among them, compound 3d and compound 3m showed strong potent anticancer activity, which were proved by that 3d: IC50 = 1.31 mu M for MCF-7 and IC50 = 0.45 mu M for WM266.5, IC50 = 0.22 mu M for BRAF(V600E), 3m: IC50 = 0.97 mu M for MCF-7 and IC50 = 0.72 mu M for WM266.5, IC50 = 0.46 mu M for BRAF(V600E), which were comparable with the positive control Erlotinib. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.020
• 作为产物：
  描述：

  4-溴苯乙酮 、 5-溴水杨醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以70%的产率得到3-(5-bromo-2-hydroxyphenyl)-1-(4-bromophenyl)prop-2-en-1-one
  参考文献：
  名称：

  开发新的查耳酮和4H-色烯作为癌症治疗剂

  摘要：

  查尔酮和色烯衍生物是通过使用无毒溶剂（例如水和乙醇）和高产率的醛醇缩合进行的简单有效的反应以高收率合成的。通常，反应在室温下进行，从而导致高纯度化合物的分离。在乳腺癌细胞（MCF-7和Hs578T）和乳腺癌非肿瘤细胞（MCF-10A）上测试了这些化合物。测定IC 50之后值，进行了专门的分析以分析这些化合物的潜力，与甲氧基或甲基相比，那些带有卤代取代基的化合物具有增强的活性。更具体地说，溴原子通常存在于进行最终测定的生物活性分子中，并被证明是有希望进行进一步研究的候选物。所选色烯充当细胞迁移抑制剂，并触发与G 2 / M细胞逮捕和微管失稳相关的受调控的细胞死亡。对于查耳酮，结果表明具有抗增殖活性。同样，联合疗法的结果增强了阿霉素的抗肿瘤作用并降低了MCF-10A细胞的细胞毒性。

  DOI：

  10.1016/j.ejmech.2018.07.058

文献信息

• Reformatsky Reaction of 1-Aryl-3-(2-hydroxyphenyl)prop-2-en-1-ones with Methyl 1-Bromocyclohexanecarboxylate
  作者：E. A. Nikiforova、D. V. Baibarodskikh、N. F. Kirillov、M. V. Dmitriev、D. P. Zverev

  DOI：10.1134/s1070428020120040

  日期：2020.12

  Abstract 1-Aryl-3-(2-hydroxy-5-R-phenyl)prop-2-en-1-ones reacted with the Reformatsky reagent derived from methyl 1-bromocyclohexanecarboxylate to give 4-(2-aryl-2-oxoethyl)-6-R-2H,4H-spiro[[1]benzopyran-3,1′-cyclohexan]-2-ones. The products are formed as a result of intramolecular cyclization of the adduct of the organozinc reagent and substituted chalcone via nucleophilic attack of the phenoxide

  摘要 1-芳基-3-（2-羟基-5-R-苯基）丙-2-烯-1-酮与衍生自1-溴环己烷甲酸甲酯的Reformatsky试剂反应生成4-（2-芳基-2-氧代乙基） -6-R-2 H，4 H-螺[[1]苯并吡喃-3,1'-环己基] -2-酮。产物是由于有机锌试剂和取代的查尔酮通过酚盐氧原子对酯羰基碳原子的亲核攻击而在分子内环化的结果而形成的。没有检测到由于烯醇盐氧原子攻击酯羰基碳原子而引起的环化产物。
• Reformatsky Reaction of Methyl 1-Bromocyclopentane-1-carboxylate with 1-Aryl-3-(2-hydroxyphenyl)prop-2-en-1-ones
  作者：E. A. Nikiforova、D. V. Baibarodskikh、N. F. Kirillov、M. V. Dmitriev、S. N. Shurov

  DOI：10.1134/s1070428019030114

  日期：2019.3

  Reformatsky reaction of methyl 1-bromocyclopentanecarboxylate with 1-aryl-3-(2-hydroxyphenyl)-prop-2-en-1-ones afforded 6-substituted 4-(2-aryl-2-oxoethyl)-2H,4H-spiro[chromene-3,1′-cyclopentan]-2-ones. A probable reaction mechanism was proposed on the basis of DFT/TZVP quantum chemical calculations.

  1-溴环戊烷甲酸甲酯与1-芳基-3-（2-羟基苯基）-丙-2-烯-1-酮的重整反应，得到6-取代的4-（2-芳基-2-氧代乙基）-2 H，4 H -螺环[chromene-3,1'-cyclopentan] -2-ones。在DFT / TZVP量子化学计算的基础上，提出了一种可能的反应机理。
• Synthesis of Spiro- and Fused Heterocycles via (4+4) Annulation of Sulfonylphthalide with<i>o</i>-Hydroxystyrenyl Derivatives
  作者：Alati Suresh、Thekke V. Baiju、Tarun Kumar、Irishi N. N. Namboothiri

  DOI：10.1021/acs.joc.8b03039

  日期：2019.3.15

  expedient one-pot protocol for the synthesis of functionalized benzofuran containing fused and spiro-heterocycles has been accomplished by the modified Hauser–Kraus (HK) annulation of sulfonylphthalide with o-hydroxychalcones and o-hydroxynitrostyrylisoxazoles. The multicascade process involves Michael addition, Dieckmann cyclization, and a series of cyclizations, eliminations, and rearrangements to deliver

  简便的一锅法合成含有稠合和螺杂环的官能化苯并呋喃的方法是，通过磺化邻苯二甲酰的邻位羟基查耳酮和邻位羟基硝基苯乙烯基恶唑修饰的Hauser-Kraus（HK）环化反应来完成。多级联过程涉及迈克尔加成，狄克曼环化以及一系列环化，消除和重排，以提供稠合的和螺杂环的产物。稠合的茚并呋喃向萘醌（一种经典的HK加合物）的不寻常转化，揭示了合成不对称萘醌的新途径。
• Diastereoselective Synthesis of Chromenopyrrole Derivative Enabled by Multicomponent Reaction of Isocyanide, Allenoate, and Phenol
  作者：Dong Li、Zhishuang Wang、Hualin Zhang、Ningyi Lu、Lei Cui、Ningmin Wu、Chunju Li、Jian Li

  DOI：10.1002/adsc.202200790

  日期：2022.9.20

  We report here an isocyanide-based multicomponent reaction to assemble a number of tricyclic chromenopyrrole derivatives with diastereoselectivity. Mechanistically, this protocol employs phenol as electron-rich species, thus following bicyclization process to approach a series of diverse structures.

  我们在这里报告了一种基于异氰化物的多组分反应，以组装许多具有非对映选择性的三环色并吡咯衍生物。在机械上，该协议采用苯酚作为富电子物种，因此遵循双环化过程来接近一系列不同的结构。
• Organocatalyzed Michael–Michael Cascade Reaction: Asymmetric Synthesis of Polysubstituted Chromans
  作者：Zhen-Xin Jia、Yong-Chun Luo、Xi-Na Cheng、Peng-Fei Xu、Yu-Cheng Gu

  DOI：10.1021/jo400476b

  日期：2013.7.5

  An enantioselective cascade Michael Michael reaction between chalcones enolates and nitromethane catalyzed by a bifunctional thiourea is developed. This reaction provides a mild but efficient approach to chiral benzopyrans bearing three consecutive stereocenters in high yields with excellent stereoselectivities, and the benzopyrans can be easily transformed to the corresponding tricyclic product.