3-(3,4-dichlorophenyl)-1-(3,4-dimethoxyphenyl)propenone | 178551-80-9

• 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-(3,4-dichlorophenyl)-1-(3,4-dimethoxyphenyl)propenone
• 英文别名: (E)-3-(3,4-dichlorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one
• CAS: 178551-80-9
• 化学式: C₁₇H₁₄Cl₂O₃
• 分子量: 337.202
• InChiKey: KAROQBDWJPUYLH-QPJJXVBHSA-N

物化性质

• 熔点：
  122-123 °C
• 沸点：
  493.4±45.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3,4-dichlorophenyl)-1-(3,4-dimethoxyphenyl)propenone 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 生成 cis-3-(3,4-dichlorophenyl)-5,6-dimethoxyindan-1-ol
  参考文献：
  名称：

  Design, Synthesis, and Monoamine Transporter Binding Site Affinities of Methoxy Derivatives of Indatraline

  摘要：

  A series of methoxy-containing derivatives of indatraline 13a-f and 17 were synthesized, and their binding affinities for the dopamine, serotonin, and norepinephrine transporter binding sites were determined. Introduction of a methoxy group to indatraline affected its affinity and selectivity greatly. Except for the 4-methoxy derivative 13a,which had the same high affinity at the dopamine transporter binding site as indatraline, the other methoxy-containing analogues (13b-f and 17) exhibited lower affinity than indatraline for the three transporter binding sites. However, some of the analogues were more selective than indatraline, and the B-methoxy derivative 13c displayed the highest affinity for both the serotonin and norepinephrine transporters. This compound retained reasonable affinity for the dopamine transporter and is a promising template for the development of a long-acting inhibitor of monoamine transporters. Such inhibitors have potential as medications for treatment, as a substitution medication, or for prevention of the abuse of methamphetamine-like stimulants.

  DOI：

  10.1021/jm000329v
• 作为产物：
  描述：

  3,4-二氯苯甲醛 、 3,4-二甲氧基苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 3-(3,4-dichlorophenyl)-1-(3,4-dimethoxyphenyl)propenone
  参考文献：
  名称：

  查尔酮衍生物靶向有丝分裂：合成，抗肿瘤活性和亲脂性评估。

  摘要：

  这项研究描述了一系列查耳酮的合成，包括吡唑和α，β-环氧衍生物，并评估了它们在三种人类肿瘤细胞系中的细胞生长抑制活性以及使用脂质体作为仿生膜模型的亲脂性。建立了合成的查耳酮的结构-活性和结构-亲脂性关系。从这项工作中，鉴定出九个查耳酮（3、5、9、11、15-19），其显示出具有有效的生长抑制活性的合适的类药物亲脂性，为化合物15-17的生长抑制作用，具有明显的抗有丝分裂作用。化合物15-17影响纺锤体装配，因此，使NCI-H460细胞中期停滞的细胞停滞，最终导致细胞死亡。在测试的化合物中，如通过有丝分裂指数计算所揭示的，化合物15表现出最高的抗有丝分裂活性。此外，15能够增强肿瘤细胞对NCI-H460细胞中低剂量紫杉醇的化学敏感性。结果表明，15通过影响微管并在有丝分裂停滞后引起细胞死亡而发挥其抗增殖活性，因此具有抗肿瘤活性的潜力。

  DOI：

  10.1016/j.ejmech.2019.111752

文献信息

• Synthesis and structural elucidation of pyrimido-[1,2-<i>a</i>]benzimidazoles and fused derivatives. i. dihydropyrimido[1,2-<i>a</i>]benzimidazoles
  作者：Dalai Abou El Ella、Edith Gößnitzer、Winfried Wendelin

  DOI：10.1002/jhet.5570330228

  日期：1996.3

  The condensation of 2-benzimidazolarnine (4, BIA) with α,β-unsaturated ketones 1 affords, according to Desenko, Orlov et al. [12,13], 1,4-dihydropyrimido[1,2-a]benzimidazoles (1,4-DHPBI, 5I). However, the described ring closure reactions could a priori also yield isomeric 1,2-DHPBI 8I or tautomers of DHPBIs 5I and 8I. An unequivocal proof for the postulated structures 5I was not presented. We prepared

  根据Desenko，Orlov等人的说法，2-苯并咪唑氮丙氨酸（4，BIA）与α，β-不饱和酮1的缩合反应。[12，13]，1，4-二氢嘧啶基[1，2- a ]苯并咪唑（1，4- DHPBI，5I）。然而，所描述的闭环反应也可以事先产生异构的1,2- DHPBI 8I或DHPBI 5I和8I的互变异构体。没有提出假定结构5I的明确证据。我们制备，如所描述的[12,13]，BIA -chalcone-和BIA -benzalacetone缩合物X和Y，5A，电子或8a，e，以及它们的盐酸盐。一维和二维高分辨率NMR分析表明，仅生成了异构体5a，e和盐5a，e ·HCl。在DMSO-d 6中，这些异构体仅以1,4-二氢互变异构体5a，eI和5a，eI ·HCl的形式存在。在三氟乙酸3,4-二氢互变异构体5α，EIII ·CF 3 COOH除了互变异构体的图5a，EI·CF 3 COOH（≈1：
• Chalcone derivatives targeting mitosis: synthesis, evaluation of antitumor activity and lipophilicity
  作者：Patricia Pinto、Carmen Mariana Machado、Joana Moreira、José Diogo P. Almeida、Patrícia M.A. Silva、Ana C. Henriques、José X. Soares、Jorge A.R. Salvador、Carlos Afonso、Madalena Pinto、Hassan Bousbaa、Honorina Cidade

  DOI：10.1016/j.ejmech.2019.111752

  日期：2019.12

  This study describes the synthesis of a series of chalcones, including pyrazole and α,β-epoxide derivatives, and evaluation of their cell growth inhibitory activity in three human tumor cell lines, as well as their lipophilicity using liposomes as a biomimetic membrane model. Structure-activity and structure-lipophilicity relationships were established for the synthetized chalcones. From this work

  这项研究描述了一系列查耳酮的合成，包括吡唑和α，β-环氧衍生物，并评估了它们在三种人类肿瘤细胞系中的细胞生长抑制活性以及使用脂质体作为仿生膜模型的亲脂性。建立了合成的查耳酮的结构-活性和结构-亲脂性关系。从这项工作中，鉴定出九个查耳酮（3、5、9、11、15-19），其显示出具有有效的生长抑制活性的合适的类药物亲脂性，为化合物15-17的生长抑制作用，具有明显的抗有丝分裂作用。化合物15-17影响纺锤体装配，因此，使NCI-H460细胞中期停滞的细胞停滞，最终导致细胞死亡。在测试的化合物中，如通过有丝分裂指数计算所揭示的，化合物15表现出最高的抗有丝分裂活性。此外，15能够增强肿瘤细胞对NCI-H460细胞中低剂量紫杉醇的化学敏感性。结果表明，15通过影响微管并在有丝分裂停滞后引起细胞死亡而发挥其抗增殖活性，因此具有抗肿瘤活性的潜力。
• Design, Synthesis, and Monoamine Transporter Binding Site Affinities of Methoxy Derivatives of Indatraline
  作者：Xiao-Hui Gu、Han Yu、Arthur E. Jacobson、Richard B. Rothman、Christina M. Dersch、Clifford George、Judith L. Flippen-Anderson、Kenner C. Rice

  DOI：10.1021/jm000329v

  日期：2000.12.1

  A series of methoxy-containing derivatives of indatraline 13a-f and 17 were synthesized, and their binding affinities for the dopamine, serotonin, and norepinephrine transporter binding sites were determined. Introduction of a methoxy group to indatraline affected its affinity and selectivity greatly. Except for the 4-methoxy derivative 13a,which had the same high affinity at the dopamine transporter binding site as indatraline, the other methoxy-containing analogues (13b-f and 17) exhibited lower affinity than indatraline for the three transporter binding sites. However, some of the analogues were more selective than indatraline, and the B-methoxy derivative 13c displayed the highest affinity for both the serotonin and norepinephrine transporters. This compound retained reasonable affinity for the dopamine transporter and is a promising template for the development of a long-acting inhibitor of monoamine transporters. Such inhibitors have potential as medications for treatment, as a substitution medication, or for prevention of the abuse of methamphetamine-like stimulants.