1-(5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-6-yl)ethanone | 31771-72-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-(5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-6-yl)ethanone
• 英文别名: 1-[5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-6-yl]ethanone；6-acetyl-5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-chromene；6-acetyl-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-5-ol；1-[5-Hydroxy-2-methyl-2-(4-methylpent-3-enyl)chromen-6-yl]ethanone
• CAS: 31771-72-9
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: BUACBPXUZNEABJ-UHFFFAOYSA-N

物化性质

• 沸点：
  417.6±45.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-6-yl)ethanone 在 一水合肼 作用下， 反应 10.0h， 生成 1-(3-(5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-6-yl)-5-(pyridin-3-yl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone
  参考文献：
  名称：

  Synthesis, Structure–Activity Relationships, and Biological Studies of Chromenochalcones as Potential Antileishmanial Agents

  摘要：

  Antileishmanial activities of a library of synthetic chalcone analogues have been examined. Among them, five compounds (11, 14, 16, 17, 22, and 24) exhibited better activity than the marketed drug miltefosine in in vitro studies against the intracellular amastigotes form of Leishmania donovani. Three promising compounds, 16, 17, and 22, were tested in a L. donovani/hamster model. Oral administration of chalcone 16, at a concentration of 100 mg/kg of body weight per day for 5 consecutive days, resulted in >84% parasite inhibition at day 7 post-treatment and it retained the activity until day 28. The molecular and immunological studies revealed that compound 16 has a dual nature to act as a direct parasite killing agent and as a host immunostimulant. Pharmacokinetics and serum albumin binding studies also suggest that compound 16 has the potential to be a candidate for the treatment of the nonhealing form of leishmaniasis.

  DOI：

  10.1021/jm401893j
• 作为产物：
  描述：

  5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromene-6-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 16.0h， 生成 1-(5-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-6-yl)ethanone
  参考文献：
  名称：

  Synthesis of Spinochalcone B and Analogues

  摘要：

  An efficient synthesis of spinochalcone B and its analogues is achieved from readily available 2H-pyran.

  DOI：

  10.1080/00397910600634316

文献信息

• Synthesis and Insight into the Structure–Activity Relationships of Chalcones as Antimalarial Agents
  作者：Narender Tadigoppula、Venkateswarlu Korthikunta、Shweta Gupta、Papireddy Kancharla、Tanvir Khaliq、Awakash Soni、Rajeev Kumar Srivastava、Kumkum Srivastava、Sunil Kumar Puri、Kanumuri Siva Rama Raju、Wahajuddin、Puran Singh Sijwali、Vikash Kumar、Imran Siddiqi Mohammad

  DOI：10.1021/jm300588j

  日期：2013.1.10

  licorice, is the most promising antimalarial compound reported so far. In continuation of our drug discovery program, we isolated two similar chalcones, medicagenin (II) and munchiwarin (III), from Crotalaria medicagenia, which exhibited antimalarial activity against Plasmodium falciparum. A library of 88 chalcones were synthesized and evaluated for their in vitro antimalarial activity. Among these, 67,

  从中国甘草的根中分离得到的Licochalcone A（I）是迄今为止报道的最有前途的抗疟化合物。在继续我们的药物发现计划时，我们从猪屎豆属中分离了两个类似的查耳酮，medicageninin（II）和munchiwarin（III），它们对恶性疟原虫具有抗疟活性。合成了88个查耳酮的文库，并对其体外抗疟活性进行了评估。在这些中，67，68，74，77，和78显示出在体外对抗疟疾活性良好恶性疟原虫具有低细胞毒性的3D7和K1菌株。这些查耳酮还显示出寄生虫约瑟氏疟原虫（N-67株）感染的瑞士小鼠的寄生虫病减少和存活时间增加。药代动力学研究表明，不良的ADME特性导致口服生物利用度低。分子对接研究揭示了这些抑制剂在falcipain-2（FP-2）酶的活性位点的结合方向。化合物67，68，和78显示出对主要血红蛋白降解半胱氨酸适度抑制活性蛋白酶FP-2。
• New Synthetic Routes to Biologically Interesting Geranylated Flavanones and Geranylated Chalcones: First Total Synthesis of (±)-Prostratol F, Xanthoangelol, and (±)-Lespeol
  作者：Doo Hwan Jung、Yong Rok Lee、Sung Hong Kim

  DOI：10.1002/hlca.200900251

  日期：2010.4

  biologically interesting geranylated flavanones and geranylated chalcones is described. Thus, the first total syntheses of the geranylated flavanones (±)‐prostratol F (1), (±)‐8‐geranyl‐3′,4′,7‐trihydroxyflavanone (2), and (±)‐6‐geranyl‐5,7‐dihydroxy‐3′,4′‐dimethoxyflavanone (3) were carried out starting from 2,4‐dihydroxyacetophenone (10) and 2,4,6‐trihydroxyacethophenone (17) in five to six steps (Schemes 2

  描述了一种新的，高效的合成方法，可用于生物学上有趣的Geranylated黄烷酮和Geranylated查耳酮。因此，首先合成了香叶基黄烷酮（±）-炔雌醇F（1），（±）-8-香叶基3'，4'，7-三羟基黄酮（2）和（±）-6-香叶基-从2,4-二羟基苯乙酮（10）和2,4,6-三羟基苯乙酮（17）开始以5至6个步骤进行5,7-dihydroxy-3'，4'-dimethoxyflavanone（3）（方案2和3）。香叶基查尔酮黄蒽酚（4），3-香叶基-2-3,3 '，4,4'-四羟基查尔酮（5），（±）-莱斯皮醇（6），以及lespeol衍生物（±） - 7 - 9合成由2,4-二羟基苯乙酮（起始10在三到四个步骤（）方案2和6）。
• Design, synthesis, and evaluation of benzofuran-based chromenochalcones for antihyperglycemic and antidyslipidemic activities
  作者：Venkateswarlu Korthikunta、Rohit Singh、Rohit Srivastava、Jyotsana Pandey、Atul Srivastava、Upma Chaturvedi、Akansha Mishra、Arvind K. Srivastava、Akhilesh K. Tamrakar、Narender Tadigoppula

  DOI：10.1039/d2md00341d

  日期：——

  Novel dual acting benzofuran-based chromenochalcones were synthesized and assessed for in vitro and in vivo antihyperglycemic and antidyslipidemic activities.

  合成了新型双效苯并呋喃类铬喹酮，并对其体内外抗高血糖和抗血脂活性进行了评估。
• Mohamed, Salah E. N.; Thomas, Philip; Whiting, Donald A., Journal of the Chemical Society. Perkin transactions I, 1987, p. 431 - 438
  作者：Mohamed, Salah E. N.、Thomas, Philip、Whiting, Donald A.

  DOI：——

  日期：——
• Synthesis of chromenochalcones and evaluation of their in vitro antileishmanial activity
  作者：Tadigoppula Narender、Tanvir Khaliq、Shweta、Nishi、Neena Goyal、Suman Gupta

  DOI：10.1016/j.bmc.2005.07.005

  日期：2005.12

  A large number of novel chromenochalcones were synthesized by pyridine-catalysed chromenylation of mono-chelated meta-dihydric acetophenones with the monoterpene, citral dimethyl acetal and subsequent Claisen-Schmidt condensation of the resultant acylchromenes with appropriate aromatic aldehydes. These chromenochalcones 1-19 were screened against in vitro extracellular promastigotes and intracellular amastigotes of Leishmania donovani. The most potent Compound in this series was compound 9 with a pyridine ring-A, which showed 99% inhibition of promastigotes at 10 mu g/ml, 82% at 0.25 mu g/ml and 96% at 10 mu g/ml concentration against amastigotes. (c) 2005 Elsevier Ltd. All rights reserved.