6-(3-methylbut-2-enyloxy)-2H-1-benzopyran-2-one | 92190-33-5

• 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
• 英文名称: 6-(3-methylbut-2-enyloxy)-2H-1-benzopyran-2-one
• 英文别名: 6-((3-methylbut-2-en-1-yl)oxy)-2H-chromen-2-one；6-isopentenyloxycoumarin；6-<3-Methyl-but-2-en-yloxy>-chromen-2-on；6-(3-methylbut-2-enoxy)chromen-2-one
• CAS: 92190-33-5
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: RFWGKRIJHGAIAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  6-(3-methylbut-2-enyloxy)-2H-1-benzopyran-2-one 在 selenium(IV) oxide 、 铜 、 对苯二酚 、 锌 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 60.0h， 生成 6-<(E)-3-(2,3,4,5-tetrahydro-4-methylidene-5-oxofuran-2-yl)but-2-enyloxy>-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Geiparvarin Analogues: Synthesis and Anticancer Evaluation ofα-Methylidene-γ-butyrolactone-Bearing Coumarins

  摘要：

  To determine some of the structural features of geiparvarin that account for its cytostatic activity in vitro, certain geiparvarin analogues modified in the furan-3(2H)-one moiety and the alkenyloxy substituent were synthesized and tested against the growth of 60 human cancer cell lines derived from nine cancer-cell types. These compounds demonstrated a strong growth-inhibitory activity against leukemia cell lines but were relatively inactive against non-small-cell lung cancers and CNS cancers. Comparison of the mean log GI, values of gamma-[(E)-1-methylprop-1-enyl]-alpha-methylidene-gamma-butyrolactones 7-9 revealed that 7-[(E)-3-(2,3,4,5-tetrahydro-4-methylidene-5-oxofuran-2-yl)but-2-enyloxy]-2H-1-benzopyran-2-one (8: - 5.47) was more active than its 6-substituted counterpart 7 (- 5.21) and its 3-chloro-4-methyl derivative 9 (- 5.31) and had a potency similar to that of geiparvarin (log GI(50) = - 5.41). These results indicated that the furan-3(2H)-one moiety of geiparvarin could be replaced by an alpha-methylidene-gamma-butyrolactone unit without losing the anticancer potency, (:nd that the best substitution site at the coumarin moiety was C(7). The alkenyloxy substituent of 8 was also replaced by a methoxy substituent. Among these alpha-methylidene-gamma-butyrolactones, 7-[(2,3,4,5-tetrahydro-4-methylidene-5-oxo-2-phenyliuran-2-yl)methoxy]-2H-1-benzopyran-2-one (1l) was the most potent with a mean log GI(50) value of - 5.83 and a range value of 132(10(212)).

  DOI：

  10.1002/(sici)1522-2675(19990210)82:2<191::aid-hlca191>3.0.co;2-p
• 作为产物：
  描述：

  6-羟基香豆素 、 1-溴-3-甲基-2-丁烯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 14.5h， 生成 6-(3-methylbut-2-enyloxy)-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Coumarin derivatives for cancer therapy

  摘要：

  本公开提供使用6-取代香豆素衍生物治疗和预防癌症的方法和组合物。本公开的香豆素衍生物在6位具有五个或更多碳原子的取代基。香豆素衍生物可能进一步取代，并且可能是3,4-二氢香豆素。在首选实施例中，本公开的香豆素衍生物用于治疗胰腺癌。

  公开号：

  US09388155B1

文献信息

• Coumarin derivatives for cancer therapy
  申请人：Wellesley College

  公开号：US09388155B1

  公开（公告）日：2016-07-12

  The disclosure provides methods and compositions for treating and preventing cancer using 6-substituted coumarin derivatives. The coumarin derivatives of the disclosure have substituents at the 6-position with five carbon atoms or greater. The coumarin derivatives may be further substituted and may be 3,4-dihydrocoumarins. In preferred embodiments, the coumarin derivatives of the disclosure are used to treat pancreatic cancer.

  本公开提供使用6-取代香豆素衍生物治疗和预防癌症的方法和组合物。本公开的香豆素衍生物在6位具有五个或更多碳原子的取代基。香豆素衍生物可能进一步取代，并且可能是3,4-二氢香豆素。在首选实施例中，本公开的香豆素衍生物用于治疗胰腺癌。
• Compositions and methods of making polymerizing nucleic acids
  申请人：The Regents of the University of California

  公开号：US11072681B2

  公开（公告）日：2021-07-27

  Provided herein are compositions and methods of making high density nucleic acid polymers.

  本文提供了制作高密度核酸聚合物的组合物和方法。
• Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors
  作者：Mehrdad Iranshahi、Atena Jabbari、Ala Orafaie、Robabeh Mehri、Soudabeh Zeraatkar、Taraneh Ahmadi、Maliheh Alimardani、Hamid Sadeghian

  DOI：10.1016/j.ejmech.2012.09.006

  日期：2012.11

  All of the mono isopentenyloxy, -geranyloxy and -farnesyloxy derivatives of coumarin were synthesized and their inhibitory potency against soybean 15-lipoxygenase (SLO) and human 15-lipoxygenase-1 (HLO-1) were determined. Amongst the synthetic analogs, 5-farnesyloxycoumarin showed the most potent inhibitory activity against SLO (IC50 = 0.8 mu M) while 6-farnesyloxycoumarin was the strongest HLO-1 inhibitor (IC50 = 1.3 mu M). The IC50 variations of the farnesyl derivatives for HLO-1 (1.3 to similar to 75 mu M) were much higher than that observed for SLO (0.8-5.8 mu M). SAR studies showed that hydrogen bonding, CH/pi, anion-pi and S-O=C interactions with Fe-III-OH, Leu408, Glu357 and Met419 were the distinct intermolecular interactions which can lead to important role of the coumarin substitution site in HLO-1 inhibitory potency, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.
• COMPOSITIONS AND METHODS OF MAKING POLYMERIZING NUCLEIC ACIDS
  申请人：The Regents of the University of California

  公开号：US20170327633A1

  公开（公告）日：2017-11-16

  Provided herein are compositions and methods of making high density nucleic acid polymers.
• US9388155B1
  申请人：——

  公开号：US9388155B1

  公开（公告）日：2016-07-12