3-(5-bromo-2-hydroxyphenyl)-1-(p-tolyl)prop-2-en-1-one | 41377-11-1

• 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-(p-tolyl)prop-2-en-1-one
• 英文别名: 5-Brom-2-hydroxy-4'-methyl-chalkon；5-bromo-2-hydroxy-4'-methyl-chalcone；3-(5-bromo-2-hydroxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one
• CAS: 41377-11-1
• 化学式: C₁₆H₁₃BrO₂
• 分子量: 317.182
• InChiKey: ZSUBZRVGYKESBB-UHFFFAOYSA-N

物化性质

• 熔点：
  188 °C (decomp)
• 沸点：
  462.8±45.0 °C(Predicted)
• 密度：
  1.437±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(5-bromo-2-hydroxyphenyl)-1-(p-tolyl)prop-2-en-1-one 在 一水合肼 作用下， 反应 8.0h， 生成 4-bromo-2-[3-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-5-yl]phenol
  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：

  对甲基苯乙酮 、 5-溴水杨醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以87%的产率得到3-(5-bromo-2-hydroxyphenyl)-1-(p-tolyl)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。
• An Access to Highly Functionalized Dihydrobenzofuran Spirooxindole Scaffolds
  作者：Daqian Wang、Jing Sun、Ying Han、Qiu Sun、Chao-Guo Yan

  DOI：10.1021/acs.orglett.2c03123

  日期：2022.10.28

  dihydrobenzofuran spirooxindole scaffolds via base promoted cascade annulation of Morita–Baylis–Hillman (MBH) carbonates of isatins with ortho-hydroxychalcones or ortho-hydroxy-β-nitrostyrenes. The complex polycyclic compounds were conveniently synthesized in satisfactory yields and with high diastereoselectivity. This protocol provides a swift and convenient approach for the assembly of diverse highly functionalized

  我们开发了一种有效的方案，用于通过碱促进的 Morita-Baylis-Hillman (MBH) 碳酸盐与邻羟基查耳酮或邻羟基-β-硝基苯乙烯的碳酸盐的碱促进级联环化来构建多环二氢苯并呋喃螺氧吲哚支架。复杂的多环化合物以令人满意的收率和高非对映选择性方便地合成。该协议为组装各种高度功能化的二氢苯并呋喃螺氧吲哚提供了一种快捷方便的方法，并且还具有广泛的底物范围、高分子收敛性和出色的原子经济性。
• Ludwig; Feuerstein; v. Kostanecki, Chemische Berichte, 1898, vol. 31, p. 714 Anm.
  作者：Ludwig、Feuerstein、v. Kostanecki

  DOI：——

  日期：——
• Synthesis of Chromenopyrroles (Azacoumestans) from Functionalized Enones and Alkyl Isocyanoacetates
  作者：Bubul Das、Anjali Dahiya、Nikita Chakraborty、Bhisma K. Patel

  DOI：10.1021/acs.orglett.3c01655

  日期：2023.7.21