4-[(1E)-3-(3,4-dimethoxyphenyl)-3-oxoprop-1-en-1-yl]benzoic acid | 119568-10-4

• 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: 4-[(1E)-3-(3,4-dimethoxyphenyl)-3-oxoprop-1-en-1-yl]benzoic acid
• 英文别名: (E)-4-(3-(3,4-dimethoxyphenyl)-3-oxoprop-1-en-1-yl)benzoic acid；4-[(E)-3-(3,4-dimethoxyphenyl)-3-oxo-prop-1-enyl]benzoic acid；4-[(E)-3-(3,4-dimethoxyphenyl)-3-oxoprop-1-enyl]benzoic acid
• CAS: 119568-10-4
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: OLYUYUJVNSXGGP-WEVVVXLNSA-N

物化性质

• 熔点：
  208.5-209.5 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  533.1±50.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(1E)-3-(3,4-dimethoxyphenyl)-3-oxoprop-1-en-1-yl]benzoic acid 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 4-[(E)-3-(3,4-Dimethoxy-phenyl)-3-oxo-propenyl]-benzoyl chloride
  参考文献：
  名称：

  细胞毒性N- [4-（3-芳基-3-氧代-1-丙烯基）苯基羰基] -3,5-双（苯基亚甲基）-4-哌啶酮和相关化合物。

  摘要：

  制备了一系列的4-羧基查耳酮1并将其与3,5-双（苯基亚甲基）-4-哌啶酮（2）偶联，产生了一系列新的N- [4-（3-芳基-3-氧代-1-） （丙烯基）苯基羰基] -3，5-双（苯基亚甲基）-4-哌啶酮（3）。酰胺3的分子简化导致形成相应的N-（3-芳基-1-氧代-2-丙烯基）-3，5-双（苯基亚甲基）-4-哌啶酮（4）。1-4系列化合物的细胞毒性评估利用了鼠P388和L1210细胞以及人Molt 4 / C8和CEM T淋巴细胞。通常，这些化合物显示出明显的毒性。当考虑所有四个筛选时，54％烯酮的IC（50）值小于10 microM，而在P388分析中，系列3的所有成员的IC（50）值小于1 microM。在系列1的化合物的效力之间建立了各种相关性 3和4以及Hammett sigma，Hansch pi和芳基取代基的分子折射率常数。通过X射线晶体学测定了系列3和4中五个代表性化合物的

  DOI：

  10.1016/s0223-5234(02)01414-9
• 作为产物：
  描述：

  对醛基苯甲酸 、 3,4-二甲氧基苯乙酮 在 potassium hydroxide 、 盐酸 作用下， 以 甲醇 为溶剂， 生成 4-[(1E)-3-(3,4-dimethoxyphenyl)-3-oxoprop-1-en-1-yl]benzoic acid
  参考文献：
  名称：

  作为潜在抗胶质母细胞瘤药物的新型螺环化合物的设计、合成和生物学评价

  摘要：

  胶质母细胞瘤（GBM）是一种侵袭性脑肿瘤，临床治疗选择极其有限。由于血脑屏障（BBB）的存在，抗GBM候选药物很难进入大脑发挥治疗作用。螺环骨架结构表现出良好的亲脂性和渗透性，使得小分子化合物能够穿过血脑屏障。在此，我们设计并合成了含有螺[3.4]辛烷环的新型3-氧杂环丁酮衍生的螺环化合物，并确定了它们在GBM细胞中抗增殖的构效关系。其中，查耳酮-螺环杂合体10m / ZS44在U251细胞中表现出高抗增殖活性和体外渗透性。此外， 10m / ZS44激活 SIRT1/p53 介导的细胞凋亡途径以抑制 U251 细胞的增殖，同时它最小程度地损害其他细胞死亡途径，例如细胞焦亡或坏死性凋亡。在小鼠异种移植模型中， 10m / ZS44对GBM肿瘤生长表现出显着的抑制作用，且未表现出明显的毒性。总体而言， 10m / ZS44代表了一种有前途的用于治疗 GBM 的螺环化合物。

  DOI：

  10.1016/j.ejmech.2023.115595

文献信息

• A chalcone derivative binds a putative allosteric site of YopH: Inhibition of a virulence factor of Yersinia
  作者：Ana C.A. de Souza、Mattia Mori、Larissa Sens、Ruth F. Rocha、Tiago Tizziani、Luiz F.S. de Souza、Louise Domeneghini Chiaradia-Delatorre、Maurizio Botta、Ricardo J. Nunes、Hernán Terenzi、Angela C.O. Menegatti

  DOI：10.1016/j.bmcl.2020.127350

  日期：2020.8

  Identification of allosteric inhibitors of PTPs has attracted great interest as a new strategy to overcome the challenge of discover potent and selective molecules for therapeutic intervention. YopH is a virulence factor of the genus Yersinia , validated as an antimicrobial target. The finding of a second substrate binding site in YopH has revealed a putative allosteric site that could be further exploited. Novel chalcone compounds that inhibit PTPs activity were designed and synthesized. Compound 3j was the most potent inhibitor, interestingly, with different mechanisms of inhibition for the panel of enzymes evaluated. Further, our results showed that com- pound 3j is an irreversible non-competitive inhibitor of YopH that binds to a site different than the catalytic site, but close to the well-known second binding site of YopH.
• Retinobenzoic acids. 2. Structure-activity relationships of chalcone-4-carboxylic acids and flavone-4'-carboxylic acids
  作者：Hiroyuki Kagechika、Emiko Kawachi、Yuichi Hashimoto、Koichi Shudo

  DOI：10.1021/jm00124a016

  日期：1989.4

  The structure-activity relationships of (E)-chalcone-4-carboxylic acids, which are retinoidal benzoic acids represented by R-Ph-X-Ph-COOH (4, X = -COCH = CH-), are discussed on the basis of differentiation-inducing activity on human promyelocytic leukemia cells HL-60. The activity was increased by the substitution of a bulky alkyl group(s) (R), and among such compounds, (E)-4-[3-(3,5-di-tert-butylphenyl)-3-oxo-1-propenyl]benzoic acid (Ch55) and (E)-4-[3-oxo-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1 -propenyl]benzoic acid (Ch80) are several times more active than retinoic acid. Though the stable conformer of chalcone derivatives is linear (s-cis form), the conformationally restricted analogue 4-(6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-4-oxonaphtho[2,3-b]py ran-2-yl)benzoic acid (Fv80) is more active than Ch80. While the effect of introduction of an oxygen atom varied, 4-[1-hydroxy-3-oxo-3-(5,6,7,8-tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2 - naphthalenyl)-1-propenyl]benzoic acid (Re80), regarded as a derivative of Ch80 with two additional hydroxyl groups, has very strong activity.
• Synthesis and in vitro biological evaluation of dihydroartemisinyl-chalcone esters
  作者：Frans J. Smit、Riëtte A. van Biljon、Lyn-Marie Birkholtz、David D. N'Da

  DOI：10.1016/j.ejmech.2014.11.016

  日期：2015.1

  A series of dihydroartemisinyl-chalcone esters were synthesized through esterification of chalcones with dihydroartemisinin (DHA). The hybrids were screened against chloroquine (CQ) sensitive (3D7) and CQ resistant (W2) strains of intraerythrocytic Plasmodium falciparum parasites, and were all found to be active, with IC50 values ranging between 1.5 and 11 nM against both strains, with SI values over 5800. The esters featuring oxygenated aryl rings (7,10 and 11), were found to be equipotent to DHA, but were 2-3 times more active than artesunate against the 3D7 and W2 strains of the malaria parasites. They were also screened in vitro against a panel of three cancer cell lines consisting of TK-10, UACC-62 and MCF-7. Compound 7, bearing a furan ring, displayed the most potent overall antitumor activity against all three cancer cell lines. TGA revealed that the targeted hybrids were all thermally more stable than DHA, which may be beneficial to the high temperature storage conditions that prevail in malaria endemic countries. During this study, ester 7 was identified as the best candidate for further investigation as a potential drug in search for new, safe and effective antimalarial drugs. (C) 2014 Elsevier Masson SAS. All rights reserved.
• USE OR RETINOIDS TO LOWER PLASMA LEVELS OF LIPOPROTEIN (a)
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0808159A1

  公开（公告）日：1997-11-26
• US5489611A
  申请人：——

  公开号：US5489611A

  公开（公告）日：1996-02-06