7-allyl-6-hydroxy-4,4,5,8-tetramethylhydrocoumarin | 219938-56-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: 7-allyl-6-hydroxy-4,4,5,8-tetramethylhydrocoumarin
• 英文别名: 7-allyl-6-hydroxy-4,4,5,8-tetramethylchroman-2-one；7-allyl-6-hydroxy-4,4,5,8-tetramethyl-3,4-dihydrocoumarin；6-hydroxy-4,4,5,8-tetramethyl-7-prop-2-enyl-3H-chromen-2-one
• CAS: 219938-56-4
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: GAWDYFPZWJGLBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  7-allyl-6-hydroxy-4,4,5,8-tetramethylhydrocoumarin 在 硼烷四氢呋喃络合物 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 生成 7-(3-hydroxy-1-propyl)-6-hydroxy-4,4,5,8-tetramethylhydrocoumarin
  参考文献：
  名称：

  用于人类乳腺癌细胞中NADPH的检测和成像的Quencher-Fluorophore型探针

  摘要：

  开发了一种新的荧光三甲基锁醌（TLQ）衍生物，称为淬灭剂-TLQ-荧光团型探针（Q-TLQ-F），用于选择性检测烟酰胺腺嘌呤二核苷酸磷酸（NADPH）。通过利用众所周知的TLQ分子内环环化反应（δ-内酯化），还原后可以释放报告分子，Q-TLQ-F成功地用于检测葡萄糖-6-磷酸产生的生理性NADPH人乳腺癌MDA-MB-231细胞中的脱氢酶。

  DOI：

  10.1002/bkcs.11826
• 作为产物：
  描述：

  3,3-二甲基丙烯酸 在 甲烷磺酸 、 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 90.0h， 生成 7-allyl-6-hydroxy-4,4,5,8-tetramethylhydrocoumarin
  参考文献：
  名称：

  用于C末端修饰肽的固相合成的氧化还原敏感树脂接头。

  摘要：

  随着使用固相合成的组合化学的迅速发展，人们对开发新的固相连接物有极大的兴趣，这些固相连接物在固相合成过程中稳定并且在温和条件下易于裂解。通过利用“三甲基锁”促进的内酯化反应，我们开发了一种氧化还原敏感性树脂接头，用于合成C末端修饰的肽。裂解仅需要温和的还原剂，例如亚硫酸氢钠，预计不会对常见的有机官能团造成任何问题。使用这个新的接头，合成了三个短肽，分离率高（70-90％）。这样的接头可潜在地用于合成修饰的肽文库，

  DOI：

  10.1021/jo981528d

文献信息

• Anti-tumuor agents
  申请人：AstraZeneca AB

  公开号：US06346633B1

  公开（公告）日：2002-02-12

  The invention concerns anti-tumour agents of formula (I) wherein each of R1, R2 and R3 has the meanings defined in the specification including hydrogen, (1-4C)alkyl, (3-4)alkenyl, (3-4C)alkynyl, amino, (1-4C)alkylamino and (1-4C)alkoxy; each of R4 and R5 is (1-4C)alkyl; each of R6 and R7 is hydrogen or (1-4C)alkyl; X is oxygen; m is 1 or 2 and each R8 is as defined in the specification; each of Y1 and Y2 is halogeno, (1-4C)alkanesulphonyloxy, benzenesulphonyloxy or phenyl-(1-4C)akanesulphonyloxy; or a pharmaceutically-acceptable salt thereof; provided that at least one of R1, R2 and R3 is other than hydrogen; a process for preparation, pharmaceutical compositions containing them and their use in the production of an anti-proliferative effect.

  该发明涉及式(I)的抗肿瘤剂，其中R1、R2和R3中的每一个具有规范中定义的含义，包括氢、(1-4C)烷基、(3-4)烯基、(3-4C)炔基、氨基、(1-4C)烷基氨基和(1-4C)烷氧基；R4和R5中的每一个是(1-4C)烷基；R6和R7中的每一个是氢或(1-4C)烷基；X是氧；m为1或2，每个R8如规范中定义；Y1和Y2中的每一个是卤素、(1-4C)烷磺酰氧基、苯磺酰氧基或苯基-(1-4C)烷磺酰氧基；或其药用可接受盐；前提是R1、R2和R3中至少有一个不是氢；一种制备方法，含有它们的药物组合物以及它们在抗增殖作用中的应用。
• Fused Heterocyclic Antioxidants: Antioxidative Activities of Hydrocoumarins in a Homogeneous Solution
  作者：Tomihiro NISHIYAMA、Junichi OHNISHI、Yasuhiro HASHIGUCHI

  DOI：10.1271/bbb.65.1127

  日期：2001.1

  We compared the antioxidative activities of seven hydrocoumarins with those of α-tocopherol for the oxidation of tetralin and linoleic acid in a homogeneous solution. Hydrocoumarins exhibited a higher induction period than that of α-Toc in both systems. However, the rate of oxygen absorption during the induction period for α-Toc was slower than that of the hydrocoumarins in both systems. In addition, 6,7-dihydroxy-4,4-dimethylhydrocoumarin showed less cytotoxicity toward human fibroblasts than did 2,6-di-t-butyl-4-methylphenol.

  我们对比了七种氢化香豆素与α-生育酚在均相溶液中对四氢萘和亚油酸氧化反应的抗氧化活性。氢化香豆素在这两个体系中显示出了比α-生育酚更长的诱导期。然而，在诱导期内，α-生育酚的氧气吸收速率在这两个体系中都比氢化香豆素慢。此外，6,7-二羟基-4,4-二甲基氢化香豆素对人类成纤维细胞的细胞毒性低于2,6-二叔丁基-4-甲基苯酚。
• Anti-tumor agents
  申请人：Astrazeneca AB

  公开号：US06472435B1

  公开（公告）日：2002-10-29

  The invention concerns anti-tumor agents of formula (I), wherein each of R1, R2 and R3 has the meanings defined in the specification including hydrogen, (1-4C)alkyl, (3-4C)alkynyl and (1-4C)alkoxyl; each of R4 and R5 is (1-4C) alkyl; each of R6 and R7 is hydrogen or (1-4C)alkyl; X is N-(1-4C)alkylimino, N-(3-4C)alkenylimino, or (3-4C)alkynylimino; m is 1 or 2 and each R8 is as defined in the specification; each Y′ and Y2 is halogen, (1-4C)alkanesulphonyloxy, benzensulphonyloxy or phenyl-(1-4C)alkanesulfonyloxy; or a pharmaceutical acceptable salt thereof; provided that at least one of R1, R2 and R3 is other than hydrogen; a process for their preparation, pharmaceutical composition containing them and their use for producing an anti-proliferative effect in a warm-blooded animal.

  该发明涉及式(I)的抗肿瘤剂，其中R1、R2和R3中的每一个具有规范中定义的含氢、(1-4C)烷基、(3-4C)炔基和(1-4C)烷氧基等含义；R4和R5中的每一个是(1-4C)烷基；R6和R7中的每一个是氢或(1-4C)烷基；X是N-(1-4C)烷基亚胺基、N-(3-4C)烯基亚胺基或(3-4C)炔基亚胺基；m为1或2，每个R8如规范中定义；每个Y'和Y2是卤素、(1-4C)烷磺酰氧基、苯基磺酰氧基或苯基-(1-4C)烷磺酰氧基；或其药学上可接受的盐；前提是R1、R2和R3中至少有一个不是氢；一种制备它们的方法，含有它们的药物组合物以及它们用于在温血动物中产生抗增殖效应的用途。
• Controlled release composition
  申请人：——

  公开号：US20020119305A1

  公开（公告）日：2002-08-29

  An alkanethiol of formula (1): HS—L—Q 1 —T—Q 2 —M—G—Z  ( 1 ), may for a SAM. Under application of a potential to the surface, the leaving group —Z is released.

  式子(1)的烷基硫醇为HS—L—Q1—T—Q2—M—G—Z，可用于自组装膜。在施加电位于表面时，离去基团—Z会被释放。
• A Novel Resin Linker for Solid-Phase Peptide Synthesis Which Can Be Cleaved Using Two Sequential Mild Reactions
  作者：Ailian Zheng、Daxian Shan、Xuling Shi、Binghe Wang

  DOI：10.1021/jo990770x

  日期：1999.10.1

  The interest in developing new linkers for solid-phase peptide and organic synthesis has increased tremendously as a result of the rapid development of combinatorial chemistry. Herein, we report the development of a new redox-sensitive linker for solid-phase peptide synthesis. This linker can be readily cleaved under mild conditions by using two sequential mild reactions, a reduction followed by a base (Bu4N+F-)-catalyzed cyclic ether formation. By using this new linker, two short peptides, a tetrapeptide [Boc-Trp-Ala-Gly-Gly-OH] and a pentapeptide [Boc-Asn-Ala-Ser(OBn)-Gly-Glu(OBn)-OH)], were synthesized. Because the cleavage does not use acidic conditions, this resin linker provides an alternative when acidic conditions are not desirable. Furthermore, the cleavage conditions do not affect most of the side chain protecting group. Therefore, the peptides synthesized can be used for the segment synthesis of larger peptides without the need to reprotect the side chain functional groups.