(E)-1-(4-chlorophenyl)-3-(2,4,5-trimethoxyphenyl)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-(4-chlorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
• 化学式: C₁₈H₁₇ClO₄
• 分子量: 332.784
• InChiKey: ZZEIAZLHMGCAHB-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-chlorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one 在 N-氯代丁二酰亚胺 、 sodium hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 27.0h， 生成 5-chloro-4-(4-chlorophenyl)-6-(2,4,5-trimethoxyphenyl)pyrimidin-2-amine
  参考文献：
  名称：

  新型嘧啶衍生物作为骨合成代谢剂通过 BMP2/SMAD1 信号通路促进成骨的设计、合成和生物学评价

  摘要：

  双膦酸盐等抗再吸收抑制剂被广泛使用，但其疗效有限且副作用严重。虽然皮下注射特立帕肽[PTH (1-34)]是一种有效的合成代谢疗法，但不建议长期重复皮下注射。今后，口服生物可利用的基于小分子的新型疗法是改善治疗的未满足的医疗需求。在这项研究中，我们设计、合成了 31 种嘧啶衍生物作为有效的骨合成代谢剂，并对其进行了生物学评价。一系列体外实验证实N- (5-溴-4-(4-溴苯基)-6-(2,4,5-三甲氧基苯基)嘧啶-2-基)己酰胺 ( 18a ) 是最有效的合成代谢剂下午 1 点。它通过激活 BMP2/SMAD1 信号通路上调成骨基因（RUNX2 和 1 型 col）的表达来促进成骨。使用体内骨折缺陷模型进一步验证了体外成骨潜力，其中化合物18a在5 mg kg -1下促进骨形成速率。我们还建立了18a的构效关系和药代动力学研究。

  DOI：

  10.1039/d3md00500c
• 作为产物：
  描述：

  顺式-2,4,5-三甲氧基-1-丙烯基苯 在 potassium permanganate 、 碳酸氢钠 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (E)-1-(4-chlorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, anticancer and antioxidant activities of 2,4,5-trimethoxy chalcones and analogues from asaronaldehyde: Structure–activity relationship

  摘要：

  2,4,5-Trimethoxy chalcones and analogues were synthesized from asaronaldehyde derived from beta-asarone. These novel compounds when tested against three human tumour cell lines (MCF-7, SW-982 and HeLa) using MTT assay, revealed that chalcones possessing electron donor groups in para position to carbonyl moiety of phenyl ring A, showed better inhibitory activity (2, 3, 4, 6, 7, 10, 17). When evaluated for antioxidant activities, compound 15 exhibited better free radical scavenging property in DPPH assay while compounds 2, 3, 5, 7, 9, 10, 11, 16, and 18 showed significant NO scavenging activity. All compounds exhibited very good phenyl hydrazine induced haemolysis of erythrocytes in phenylhydrazine assay. Structure activity relationship (SAR) study using in-silico analysis matched well with in-vitro tumour cell inhibitory activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.018

文献信息

• Synthesis, Characterization and Antimicrobial Activities of Chalcones and Their Post Transformation to Pyrazole Derivatives
  作者：D. Ramyashree、K.R. Raghavendra、A. Dileep Kumar、C.B. Vagish、K. Ajay Kumar

  DOI：10.14233/ajchem.2017.20561

  日期：——

  An efficient procedure for the synthesis of trisubstituted pyrazoles was developed. Claisen-Schmidt condensation of 2,4,5-trimethoxybenzaldehyde and substituted acetophenone in the presence of aqueous alkaline bases produced chalcones. The cyclocondensation reaction of chalcones and phenyl hydrazine hydrochloride catalyzed by an acid produced trisubstituted pyrazolines in good yields. The synthesized new compounds were characterized by spectral studies and elemental analysis and some of the intermediate chalcones by single crystal X-ray diffraction studies. The compounds were screened in vitro for their antimicrobial susceptibilities against different bacteria and fungi species.

  开发了一种合成三取代吡唑的高效工艺。在含水碱性条件下，2,4,5-三甲氧基苯甲醛与取代苯乙酮进行克莱森-施密特缩合反应，生成查耳酮。在酸催化下，查耳酮与苯肼盐酸盐发生环化缩合反应，以良好产率生成三取代吡唑啉。通过光谱研究和元素分析对合成的新化合物进行了表征，部分中间体查耳酮通过单晶X射线衍射研究进行了鉴定。对这些化合物进行了体外抗菌活性筛选，测试了它们对不同细菌和真菌种类的抗菌敏感性。
• Synthesis, anticancer and antioxidant activities of 2,4,5-trimethoxy chalcones and analogues from asaronaldehyde: Structure–activity relationship
  作者：Suvarna Shenvi、Krishna Kumar、Kaushik S. Hatti、K. Rijesh、Latha Diwakar、G. Chandrasekara Reddy

  DOI：10.1016/j.ejmech.2013.01.018

  日期：2013.4

  2,4,5-Trimethoxy chalcones and analogues were synthesized from asaronaldehyde derived from beta-asarone. These novel compounds when tested against three human tumour cell lines (MCF-7, SW-982 and HeLa) using MTT assay, revealed that chalcones possessing electron donor groups in para position to carbonyl moiety of phenyl ring A, showed better inhibitory activity (2, 3, 4, 6, 7, 10, 17). When evaluated for antioxidant activities, compound 15 exhibited better free radical scavenging property in DPPH assay while compounds 2, 3, 5, 7, 9, 10, 11, 16, and 18 showed significant NO scavenging activity. All compounds exhibited very good phenyl hydrazine induced haemolysis of erythrocytes in phenylhydrazine assay. Structure activity relationship (SAR) study using in-silico analysis matched well with in-vitro tumour cell inhibitory activity. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Design, synthesis and biological evaluation of novel pyrimidine derivatives as bone anabolic agents promoting osteogenesis <i>via</i> the BMP2/SMAD1 signaling pathway
  作者：Sumit K. Rastogi、Sonu Khanka、Santosh Kumar、Amardeep Lakra、Rajat Rathur、Kriti Sharma、Amol Chhatrapati Bisen、Rabi Sankar Bhatta、Ravindra Kumar、Divya Singh、Arun K. Sinha

  DOI：10.1039/d3md00500c

  日期：2024.2.21

  [PTH (1–34)] is an effective anabolic therapy, long-term repeated subcutaneous administration is not recommended. Henceforth, orally bio-available small-molecule-based novel therapeutics are unmet medical needs to improve the treatment. In this study, we designed, synthesized, and carried out a biological evaluation of 31 pyrimidine derivatives as potent bone anabolic agents. A series of in vitro experiments

  双膦酸盐等抗再吸收抑制剂被广泛使用，但其疗效有限且副作用严重。虽然皮下注射特立帕肽[PTH (1-34)]是一种有效的合成代谢疗法，但不建议长期重复皮下注射。今后，口服生物可利用的基于小分子的新型疗法是改善治疗的未满足的医疗需求。在这项研究中，我们设计、合成了 31 种嘧啶衍生物作为有效的骨合成代谢剂，并对其进行了生物学评价。一系列体外实验证实N- (5-溴-4-(4-溴苯基)-6-(2,4,5-三甲氧基苯基)嘧啶-2-基)己酰胺 ( 18a ) 是最有效的合成代谢剂下午 1 点。它通过激活 BMP2/SMAD1 信号通路上调成骨基因（RUNX2 和 1 型 col）的表达来促进成骨。使用体内骨折缺陷模型进一步验证了体外成骨潜力，其中化合物18a在5 mg kg -1下促进骨形成速率。我们还建立了18a的构效关系和药代动力学研究。