3,4-methylenedioxy-2',4'-dimethoxychalcone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-methylenedioxy-2',4'-dimethoxychalcone
• 英文别名: 3-(1,3-benzodioxol-5-yl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: XMQLRMQKCIIQEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  醋谷胺 、 3,4-methylenedioxy-2',4'-dimethoxychalcone 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以55%的产率得到6-(2,4-dimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-1H-pyridin-2-one
  参考文献：
  名称：

  The synthesis of 4,6-diaryl-2-pyridones and their bioactivation in CYP1 expressing breast cancer cells

  摘要：

  As part of a programme to develop anticancer prodrugs which are activated by cytochrome P450 (CYP) 1B1, a library of 4,6-diaryl-2-pyridones was synthesised in yields of 6-60% from the corresponding chalcones. A number of these derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing little toxicity towards a non-tumour breast cell line with no CYP expression. Metabolism studies provided evidence supporting the involvement of CYP1 enzymes in the bioactivation of these compounds.

  DOI：

  10.1016/j.bmcl.2019.03.030
• 作为产物：
  描述：

  胡椒醛 、 2,4-二甲氧基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.17h， 生成 3,4-methylenedioxy-2',4'-dimethoxychalcone
  参考文献：
  名称：

  QSAR，计算机对接和查尔酮衍生物作为H1N1病毒神经氨酸酶的潜在抑制剂的体外评估

  摘要：

  三十3查耳酮通过使用MUNANA测定合成和对病毒H1N1神经氨酸酶活性测试[2' - （4-甲基伞形基）-α- d - Ñ -acetylneuraminic酸]测定与DANA（2,3-二脱氢-2-脱氧Ñ-乙酰神经氨酸）作为标准。已经成功开发了2D和3D定量结构-活性关系模型，这些模型对这些查尔酮衍生物的定量结构-活性关系具有良好的相关性和预测能力。二维定量结构-活性关系模型的结果表明，静电参数增强了查耳酮的生物活性，而空间取代基减弱了其作为H1N1神经氨酸酶抑制剂的能力。3D定量结构-活性关系模型显示了查尔酮衍生物中羟基位置的重要性，该位置会影响疏水性，氢键供体和增强生物活性的芳环特征。最后，对接研究表明，查尔肯斯MC8和具有低C docker相互作用能和更多氢键键合的MC16对病毒H1N1神经氨酸酶具有更好的抑制活性。

  DOI：

  10.1007/s00044-016-1636-5

文献信息

• Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors
  作者：Mehtap TUĞRAK、Halise İnci GÜL、Hiroshi SAKAGAMİ、Rüya KAYA、İlhami GÜLÇİN

  DOI：10.3906/kim-2009-37

  日期：——

  Cancer is a disease characterized by the continuous growth of cells without adherence to the rules that healthy normal cells obey. Carbonic anhydrase I and II (CA I and CA II) inhibitors are used for the treatment of some diseases. The available drugs in the market have limitations or side effects, which bring about the need to develop new drug candidate compound(s) to overcome the problems at issue

  癌症是一种疾病，其特征是细胞不断生长，但不遵守健康的正常细胞所遵循的规则。碳酸酐酶 I 和 II（CA I 和 CA II）抑制剂用于治疗某些疾病。市场上现有的药物存在局限性或副作用，这就需要开发新的候选药物化合物来克服这些问题。在本研究中，新型吡唑-磺酰胺杂化化合物 4-[5-(1,3-benzodioxol-5-yl)-3-aryl-4,5-dihydro-1H-pyrazol-1-yl] 苯磺酰胺 (4a - 4j) 旨在发现新的候选药物化合物。合成了化合物4a-4j，并使用光谱技术确认了它们的化学结构。测试的假设是甲氧基和多甲氧基的引入是否会导致化合物的效能选择性表达 (PSE) 值增加，这反映了化合物的细胞毒性和选择性。化合物对肿瘤细胞系的细胞毒性在 6.7 - 400 µM 的范围内。化合物 4i (PSE2 = 461.5) 和 4g (PSE1 = 193.2) 在细胞毒性试验中具有最高的
• 3, 4-Methylenedioxy-substituted chalcones as therapeutic agents
  申请人：——

  公开号：US20040254149A1

  公开（公告）日：2004-12-16

  The present invention pertains to the use of a compounds for the manufacture of a medicament for use in the treatment of a proliferative condition, wherein the compounds have the following formula: 1 wherein: each of R B2 , R B3 , R B4 , and R B5 is independently —H, —OH, or —OMe; each of R 1 and R 2 is independently: —H, optionally substituted C 1-4 alkyl, or optionally substituted C 5-20 aryl; R A3 is —H, —OH, —OC(═O)R E , —OS(═O) 2 OH, or —OP(═O)(OH) 2 ; R E is: —H, optionally substituted C 1-6 alkyl, optionally substituted C 3-20 heterocyclyl, or optionally substituted C 5-20 aryl; or a pharmaceutically acceptable salt, solvate, amide, ester, ether, chemically protected form, or prodrug thereof. The present invention also pertains to such compounds, pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, for both diagnosis and treatment of, for example, proliferative conditions, such as cancer, and inflammatory conditions.

  本发明涉及使用某些化合物制备药物，用于治疗增殖性疾病，其中该化合物具有以下结构式：1其中：RB2、RB3、RB4和RB5中的每一个独立地为—H、—OH或—OMe；R1和R2中的每一个独立地为—H、选择性地取代的C1-4烷基或选择性地取代的C5-20芳基；RA3为—H、—OH、—OC(═O)RE、—OS(═O)2OH或—OP(═O)(OH)2；RE为：—H、选择性地取代的C1-6烷基、选择性地取代的C3-20杂环基或选择性地取代的C5-20芳基；或其药学上可接受的盐、溶剂化物、酰胺、酯、醚、化学保护形式或前药。本发明还涉及这些化合物、包含这些化合物的药物组成物，以及这些化合物和组成物的使用，无论是在体内还是体外，用于诊断和治疗增殖性疾病，例如癌症和炎症性疾病。
• 3,4-METHYLENEDIOXY-SUBSTITUTED CHALCONES AS THERAPEUTIC AGENTS
  申请人：Potter Gerard Andrew

  公开号：US20100028262A1

  公开（公告）日：2010-02-04

  The present invention pertains to the use of a compounds for the manufacture of a medicament for use in the treatment of a proliferative condition, wherein the compounds have the following formula: wherein: each of R B2 , R B3 , R B4 , and R B5 is independently —H, —OH, or —OMe; each of R 1 and R 2 is independently: —H, optionally substituted C 1-4 alkyl, or optionally substituted C 5-20 aryl; R A3 is —H, —OH, —OC(═O)R E , —OS(═O) 2 OH, or —OP(═O)(OH) 2 ; R E is: —H, optionally substituted C 1-6 alkyl, optionally substituted C 3-20 heterocyclyl, or optionally substituted C 5-20 aryl; or a pharmaceutically acceptable salt, solvate, amide, ester, ether, chemically protected form, or prodrug thereof. The present invention also pertains to such compounds, pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, for both diagnosis and treatment of, for example, proliferative conditions, such as cancer, and inflammatory conditions.

  本发明涉及使用化合物制备药物，用于治疗增殖性疾病，其中该化合物具有以下结构式：其中：RB2、RB3、RB4和RB5中的每一个独立地为—H、—OH或—OMe；R1和R2中的每一个独立地为—H、可选地取代的C1-4烷基或可选地取代的C5-20芳基；RA3为—H、—OH、—OC(═O)RE、—OS(═O)2OH或—OP(═O)(OH)2；RE为：—H、可选地取代的C1-6烷基、可选地取代的C3-20杂环基或可选地取代的C5-20芳基；或其药学上可接受的盐、溶剂化合物、酰胺、酯、醚、化学保护形式或前药。本发明还涉及这种化合物、包含这种化合物的药物组合物以及这种化合物和组合物的使用，无论是在体内还是体外，用于诊断和治疗增殖性疾病（例如癌症）和炎症性疾病。
• US7598294B2
  申请人：——

  公开号：US7598294B2

  公开（公告）日：2009-10-06
• [EN] 3,4-METHYLENEDIOXY-SUBSTITUTED CHALCONES AS THERAPEUTIC AGENTS<br/>[FR] CHALCONES A SUBSTITUTION 3,4-METHYLENEDIOXY UTILISEES COMME AGENTS THERAPEUTIQUES
  申请人：CANCER REC TECH LTD

  公开号：WO2003028713A2

  公开（公告）日：2003-04-10

  The present invention pertains to the use of a compound for the manufacture of a medicament for use in the treatment of a proliferative condition, wherein the compounds have the following formula (1): wherein: each of RB2, RB3, RB4, and RB5 is independently -H, -OH, or -OMe; each of R1 and R2 is independently: -H, optionally substituted C1-4alkyl, or optionally substituted C5-20aryl; RA3 is -H, -OH, -OC(=O)RE, -OS(=O)2OH, or -OP(=O)(OH)2; RE is: -H, optionally substituted C1-6alkyl, optionally substituted C3-20heterocyclyl, or optionally substituted C5-20aryl; or a pharmaceutically acceptable salt, solvate, amide, ester, ether, chemically protected form, or prodrug thereof. The present invention also pertains to such compounds, pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, for both diagnosis and treatment of, for example, proliferative conditions, such as cancer, and inflammatory conditions.