methyl 6-acetoxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate | 70859-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: methyl 6-acetoxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate
• 英文别名: 6-O-acetylmollugin；acetylmollugin；6-acetoxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylic acid methyl ester；6-Acetoxy-5-carboxymethyl-2,2-dimethyl-2H-naphtho<1,2-b>-pyran；methyl 6-acetyloxy-2,2-dimethylbenzo[h]chromene-5-carboxylate
• CAS: 70859-07-3
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: CAJUOEHGLGBBGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 6-acetoxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate 在 sodium tetrahydroborate 作用下， 生成 Acetic acid 2,2-dimethyl-6-oxo-2,3,4a,6-tetrahydro-1,4,5-trioxa-naphtho[3,2,1-cd]azulen-7-yl ester
  参考文献：
  名称：

  Itokawa, Hideji; Mihara, Kazuhiko; Takeya, Koichi, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 7, p. 2353 - 2358

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-二羟基萘 在 18-冠醚-6 、 potassium hydride 、 sodium hydride 、 丙酸 、 苯硼酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 10.17h， 生成 methyl 6-acetoxy-2,2-dimethyl-2H-benzo[h]chromene-5-carboxylate
  参考文献：
  名称：

  Facile Synthesis of Mollugin by Kinetic Control and anti-HCV (Hepatitis C Virus) Activity of Its Analogues

  摘要：

  据报道，Mollugin具有多种生物活性，包括抗肿瘤、抗病毒（针对乙型肝炎病毒）、抗衰老和抗突变活性。本文介绍了一种从廉价的起始原料1,4-萘醌出发，通过动力学控制，两步高效简洁合成Mollugin的方法，并筛选了所制备的Mollugin衍生物对丙型肝炎病毒（HCV）的抑制能力。研究表明，二氢苯并色原烯结构可能作为一种新的领先化合物，成为额外的抗HCV药物。

  DOI：

  10.5012/bkcs.2014.35.11.3232

文献信息

• Synthesis of novel and diverse mollugin analogues and their antibacterial and antioxidant activities
  作者：Akber Idhayadhulla、Likai Xia、Yong Rok Lee、Sung Hong Kim、Young-Jung Wee、Chong-Soon Lee

  DOI：10.1016/j.bioorg.2013.11.008

  日期：2014.2

  Novel and diverse mollugin analogues (1-12) were synthesized using PhB(OH)(2)/AcOH-mediated electrocyclization reaction as a key step. The newly synthesized compounds were screened for antioxidant and antibacterial activities. Compounds 1, 2, 5, 6, 8, and 10-12 showed high antioxidant activities in DPPH inhibition (IC50 = 0.52-1.11 mu M) compared with BHT (IC50 = 9.67 mu M). Compounds 3 exhibited potent antibacterial activity against Staphylococcus aureus (KCTC-1916) bacterial strain at 100 mu g/mL. Structures of newly synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR data and high-resolution mass spectrometry. (C) 2013 Elsevier Inc. All rights reserved.
• Facile Synthesis of Mollugin by Kinetic Control and anti-HCV (Hepatitis C Virus) Activity of Its Analogues
  作者：Da Hye Choi、Na Ri Lee、Cheol Gi Kim、Jong Woo Kim、Sang Wook Lee、Jong-Gab Jun

  DOI：10.5012/bkcs.2014.35.11.3232

  日期：2014.11.20

  Mollugin has been reported to have various biological activities including antineoplastic, antitumor, antiviral against the hepatitis B virus, anti-aging and antimutagenic activities. An effective and concise synthesis of mollugin in two steps including kinetic control from the cheap starting material 1,4-naphthoquinone has been introduced, and mollugin derivatives thus prepared are screened for their inhibition ability against the hepatitis C virus (HCV) and the dihydrobenzochromene structure might be an additional anti-HCV agent as a new leading compound.

  据报道，Mollugin具有多种生物活性，包括抗肿瘤、抗病毒（针对乙型肝炎病毒）、抗衰老和抗突变活性。本文介绍了一种从廉价的起始原料1,4-萘醌出发，通过动力学控制，两步高效简洁合成Mollugin的方法，并筛选了所制备的Mollugin衍生物对丙型肝炎病毒（HCV）的抑制能力。研究表明，二氢苯并色原烯结构可能作为一种新的领先化合物，成为额外的抗HCV药物。
• Itokawa, Hideji; Mihara, Kazuhiko; Takeya, Koichi, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 7, p. 2353 - 2358
  作者：Itokawa, Hideji、Mihara, Kazuhiko、Takeya, Koichi

  DOI：——

  日期：——