6-乙基-7-羟基-4-甲基-2H-色烯-2-酮 | 1484-73-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 6-乙基-7-羟基-4-甲基-2H-色烯-2-酮
• 英文名称: 6-Ethyl-7-hydroxy-4-methylcumarin
• 英文别名: 6-ethyl-7-hydroxy-4-methylcoumarin；6-ethyl-7-hydroxy-4-methyl-2H-chromen-2-one；6-ethyl-7-hydroxy-4-methylchromen-2-one
• CAS: 1484-73-7
• 化学式: C₁₂H₁₂O₃
• mdl: MFCD01106609
• 分子量: 204.225
• InChiKey: QHDTWGXIYHPUKI-UHFFFAOYSA-N

物化性质

• 熔点：
  213 °C
• 沸点：
  390.5±42.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2932209090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  6-乙基-7-羟基-4-甲基-2H-色烯-2-酮 在 三氯化铝 作用下， 反应 4.0h， 生成 8-acetyl-6-ethyl-7-hydroxy-4-methyl coumarin
  参考文献：
  名称：

  Na⁺-Glucose Cotransporter (SGLT) Inhibitors as Antidiabetic Agents. 4. Synthesis and Pharmacological Properties of 4‘-Dehydroxyphlorizin Derivatives Substituted on the B Ring

  摘要：

  In our studies of Na+-glucose cotransporter (SGLT) inhibitors as antidiabetic agents, a series of novel 4'-dehydroxyphlorizin derivatives substituted on the B ring was prepared and their effects on urinary glucose excretion were evaluated in rats. Introduction of only a small alkyl group at the 4'-position increased the activity, and 3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-beta-D-glucopyranoside (4) showed the most potent effect. To overcome hydrolysis of compound 4 by beta-glucosidase in the digestive tract, the OH groups on the glucose moiety of compound 4 were modified. Three prodrugs (5, 42, and 55) were more potent than the parent compound 4 by oral administration, and finally 3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-(6-O-methoxycarbonyl-beta-D-glucopyranoside) (5) was selected as a new promising candidate. Compound 5 was metabolized mainly by liver esterase to the active form (4), which was about 10 times more potent than 5 in inhibiting SGLT. In oral glucose tolerance test in db/db mice, compound 5 dose-dependently suppressed the elevation of glucose levels. Single administration of 5 reduced hyperglycemia concurrently with increase of glucose excretion into urine in diabetic KK-A(y) mice. Furthermore, compound 5 suppressed the elevation of blood glucose levels but did not lower it below the normal level even in fasted conditions in KK-A(y) mice. Additionally, long-term treatment with 5 dose-dependently reduced hyperglycemia and HbA1c in KK-A(y) mice. These pharmacological data strongly suggest that compound 5 has a therapeutic potential in the treatment of NIDDM.

  DOI：

  10.1021/jm990175n
• 作为产物：
  描述：

  2-乙基-5-甲氧基苯酚 在 三氯化铝 、 氢碘酸 、 乙酸酐 、 硝基苯 作用下， 生成 6-乙基-7-羟基-4-甲基-2H-色烯-2-酮
  参考文献：
  名称：

  Usgaonkar et al., Journal of the Indian Chemical Society, 1953, vol. 30, p. 535,536

  摘要：

  DOI：

文献信息

• Skeletal diversity construction via a branching synthetic strategy
  作者：Emma E. Wyatt、Suzanne Fergus、Warren R. J. D. Galloway、Andreas Bender、David J. Fox、Alleyn T. Plowright、Alan S. Jessiman、Martin Welch、David R. Spring

  DOI：10.1039/b607710b

  日期：——

  A branching synthetic strategy was used to efficiently generate structurally diverse scaffolds, which span a broad area of chemical descriptor space, and their biological activity against MRSA was demonstrated.

  一种分支合成策略被用来高效生成结构多样的骨架，覆盖了广泛的化学描述空间，并且证明了它们对耐甲氧西林金黄色葡萄球菌（MRSA）的生物活性。
• Establishing a Flow Process to Coumarin-8-Carbaldehydes as Important Synthetic Scaffolds
  作者：Jaroslav Zak、David Ron、Elena Riva、Heather P. Harding、Benedict C. S. Cross、Ian R. Baxendale

  DOI：10.1002/chem.201201039

  日期：2012.8.6

  Despite their usefulness as fluorophores and synthetic precursors, efficient and reliable routes to coumarin‐8‐carbaldehydes are lacking. We describe here a high‐yielding continuous flow synthesis that requires no manual intermediate purification or work‐up, giving access to multigram quantities of the aldehyde product.

  尽管它们可用作荧光团和合成前体，但仍缺乏高效，可靠的香豆素-8甲醛合成途径。我们在这里描述了一种高产量的连续流合成方法，不需要人工进行中间纯化或后处理，可以得到数克量的醛产品。
• Synthesis and structure-activity relationship of coumarins as potent Mcl-1 inhibitors for cancer treatment
  作者：Yang-Liu Xia、Jing-Jing Wang、Shi-Yang Li、Yong Liu、Frank J. Gonzalez、Ping Wang、Guang-Bo Ge

  DOI：10.1016/j.bmc.2020.115851

  日期：2021.1

  Myeloid cell leukemia-1 (Mcl-1) is a validated and attractive target for cancer therapy. Over-expression of Mcl-1 in many cancers allows cancer cells to evade apoptosis and contributes to their resistance to current chemotherapeutics. In this study, more than thirty coumarin derivatives with different substituents were designed and synthesized, and their Mcl-1 inhibitory activities evaluated using

  髓样细胞白血病-1 (Mcl-1) 是经过验证且有吸引力的癌症治疗靶点。 Mcl-1 在许多癌症中的过度表达使癌细胞能够逃避细胞凋亡，并有助于它们对当前化疗药物的抵抗。在本研究中，设计并合成了三十多种具有不同取代基的香豆素衍生物，并使用基于荧光偏振的结合测定评估了它们的 Mcl-1 抑制活性。结果表明，儿茶酚基团是香豆素类Mcl-1抑制活性的关键组成部分，儿茶酚基团的甲基化导致抑制活性降低。在6,7-二羟基香豆素的C-4位引入疏水性吸电子基团，增强了Mcl-1抑制能力，而在该位置引入亲水基团则不利于抑制效力。此外，在C-5或C-8位引入含氮基团，允许形成分子内氢键，也不利于Mcl-1抑制。在所有测试的香豆素中，4-三氟甲基-6,7-二羟基香豆素 (Cpd 4 ) 对 Mcl-1 显示出最有效的抑制活性（分别为K i = 0.21 ± 0.02 μM， IC 50 = 1.21 ± 0.56
• Retinoids and methods of use of same
  申请人：Institute of Materia Medica

  公开号：US05968940A1

  公开（公告）日：1999-10-19

  New purine retinoid compounds according to the formula: ##STR1## wherein R is a purine derivative, and pharmaceutical compositions thereof, are provided which exhibit cancer-inhibiting activity.

  根据以下公式提供了新的嘌呤类视黄醇化合物：##STR1## 其中R是嘌呤衍生物，并且提供了具有抗癌活性的药物组合物。
• Thakar; Pathak; Dumir, Journal of the Indian Chemical Society, 1980, vol. 57, # 1, p. 89 - 91
  作者：Thakar、Pathak、Dumir

  DOI：——

  日期：——