methylene-bis-(3,5-di-isobutanoyl-2,4,6-trihydroxybenzene) | 68223-31-4

• 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: methylene-bis-(3,5-di-isobutanoyl-2,4,6-trihydroxybenzene)
• 英文别名: 2-Methyl-1-[2,4,6-trihydroxy-3-(2-methylpropanoyl)-5-[[2,4,6-trihydroxy-3,5-bis(2-methylpropanoyl)phenyl]methyl]phenyl]propan-1-one
• CAS: 68223-31-4
• 化学式: C₂₉H₃₆O₁₀
• 分子量: 544.599
• InChiKey: PXOXCJADZPFJCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  190
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1,1',1'',1'''-(methylenebis(2,4,6-trimethoxybenzene-5,3,1-triyl))tetrakis(2-methylpropan-1-one) 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以53%的产率得到methylene-bis-(3,5-di-isobutanoyl-2,4,6-trihydroxybenzene)
  参考文献：
  名称：

  Sc(OTf)₃-Catalyzed Synthesis of Symmetrical Dithioacetals and Bisarylmethanes Using Nitromethane as a Methylene Source

  摘要：

  Use of nitromethane as an electrophilic methylene source for the synthesis of symmetrical dithioacetals and bisarylmethanes has been showcased using Sc(OTf)(3) as a catalyst. The procedure allows straightforward access to the densely functionalized dithioacetals and bisarylmethanes under mild conditions. Additionally, the method has been applied for the synthesis of antimalarial tetramethyl mellotojaponin C and anticancer dimeric phloroglucinol derivative.

  DOI：

  10.1021/acs.orglett.0c01831

文献信息

• One pot synthesis and anticancer activity of dimeric phloroglucinols
  作者：Siddheshwar K. Chauthe、Sandip B. Bharate、Giridharan Periyasamy、Amit Khanna、Kamlesh K. Bhutani、Prabhu D. Mishra、Inder P. Singh

  DOI：10.1016/j.bmcl.2012.01.089

  日期：2012.3

  were synthesized in a single step using commercially available phloroglucinol and methanesulfonic acid. Based on the reported anticancer activity of plant derived dimeric phloroglucinols, these synthesized compounds were evaluated for their in vitro anti-proliferative activities against various cancer cell lines. Several compounds demonstrated in vitro cytotoxic effects across a wide array of tumor cell

  使用市售的间苯三酚和甲磺酸可一步合成一系列二聚间苯三酚化合物。基于植物来源的二聚间苯三酚的报道的抗癌活性，评估了这些合成的化合物对各种癌细胞系的体外抗增殖活性。几种化合物在多种肿瘤细胞类型中均表现出体外细胞毒性作用。发现在结肠癌细胞系（HCT116）中，在IC 50为5.5μM的低的所有五个癌细胞系中，具有在连接基亚甲基上的吡啶-3-基和两个二异戊酰基间苯三酚部分的化合物29是最活跃的。
• Biomimetic synthesis and anti-HIV activity of dimeric phloroglucinols
  作者：Siddheshwar K. Chauthe、Sandip B. Bharate、Sudeep Sabde、Debashis Mitra、Kamlesh K. Bhutani、Inder P. Singh

  DOI：10.1016/j.bmc.2010.01.023

  日期：2010.3

  Plants are an important source of a variety of bioactive compounds with different modes of action. Anti-HIV agents from plant sources can be useful in developing novel therapies for inhibiting HIV infection. Based on the reported anti-HIV activity of plant derived phloroglucinols, several new dimeric phloroglucinols were synthesized in the present study by varying substitution on aromatic ring and

  植物是具有不同作用方式的多种生物活性化合物的重要来源。来自植物来源的抗HIV剂可用于开发抑制HIV感染的新疗法。根据已报道的植物来源的间苯三酚的抗HIV活性，通过改变芳香环和亚甲基桥上的取代基，在本研究中合成了几种新的二聚间苯三酚。一些合成的化合物在感染HIV-1 NL 4.3病毒分离株的人CD4 + T细胞系（CEM-GFP）中显示出良好的HIV抑制活性。结构活性研究表明，亚甲基桥上的苯基，4-苄氧基-1-苯基和环己基取代使化合物具有更好的抗HIV活性。化合物22和24显示出最高的抗HIV活性，IC 50分别为0.28μM和2.71μM，在基于细胞的测定中，前者的活性比阳性标准AZT高。
• Toward an efficient and eco-friendly route for the synthesis of dimeric 2,4-diacetyl phloroglucinol and its potential as a SARS-CoV-2 main protease antagonist: insight from <i>in silico</i> studies
  作者：Triana Kusumaningsih、Wahyu E. Prasetyo、Fajar R. Wibowo、Maulidan Firdaus

  DOI：10.1039/d0nj06114j

  日期：——

  effective and eco-friendly synthetic routes for the synthesis of dimeric 2,4-diacetyl phloroglucinol 4a, a potent antibiotic and malarial drug candidate via phenol–aldehyde condensation over silica sulphuric acid (SSA) catalyst and the arylation of dimethylammonium salts under greener protocols, i.e., ultrasound-assisted (US) and liquid assisted grinding (LAG) methods. Through an environmental assessment

  由于无法获得抗病毒药物SARS-CoV-2，因此在当前COVID-19大流行时代的紧急情况下，开发抗病毒药物的前景至关重要。为了支持有关COVID-19疗法改进的持久研究，我们在本文中证明了开发高效，环保的合成路线用于合成二聚2,4-二乙酰基间苯三酚4a（一种有效的抗生素和疟疾候选药物）的途径。酚-醛缩合在二氧化硅硫酸（SSA）的催化剂和甲基铵盐的下更环保的协议的芳基化，即，超声辅助（US）和液体辅助研磨（LAG）方法。通过环境评估，与最近发布的替代合成途径相比，已证明所开发规程的清洁度和环境效率得到改善，这表明存在更高的效率和更低的环境影响。此外，我们完成了分子对接研究，从而可以快速筛选4a及其衍生物以及N3，氯喹和瑞姆昔韦的可能治疗性配体，以此作为最近释放的3-胰凝乳蛋白酶样半胱氨酸蛋白酶（3CL pro（SARS-CoV-2）。排他性地，我们的发现表明化合物4d具有出色的-8.1 kcal结合亲和力的活性位点在3CL
• Sc(OTf)₃-Catalyzed Synthesis of Symmetrical Dithioacetals and Bisarylmethanes Using Nitromethane as a Methylene Source
  作者：Dattatraya H. Dethe、Manmohan Shukla、Balu D. Dherange

  DOI：10.1021/acs.orglett.0c01831

  日期：2020.8.7

  Use of nitromethane as an electrophilic methylene source for the synthesis of symmetrical dithioacetals and bisarylmethanes has been showcased using Sc(OTf)(3) as a catalyst. The procedure allows straightforward access to the densely functionalized dithioacetals and bisarylmethanes under mild conditions. Additionally, the method has been applied for the synthesis of antimalarial tetramethyl mellotojaponin C and anticancer dimeric phloroglucinol derivative.