9-羟基-8,8-二甲基-9,10-二氢-2H,8H-吡喃并[2,3-f]苯并吡喃-2-酮 | 1147-25-7

• 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: 9-羟基-8,8-二甲基-9,10-二氢-2H,8H-吡喃并[2,3-f]苯并吡喃-2-酮
• 中文别名: 9-羟基-8,8-二甲基-9,10-二氢-8H-苯并吡喃[2,3-F]-2-酮
• 英文名称: lomatin
• 英文别名: Xanthogalol；3'-hydroxy-3',4'-dihydroseselin；Xanthogallol；9-hydroxy-8,8-dimethyl-9,10-dihydropyrano[2,3-h]chromen-2-one
• CAS: 1147-25-7；19380-05-3；32279-74-6；141316-01-0
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: UJSHBYQGQRPVNO-UHFFFAOYSA-N

物化性质

• 熔点：
  183-185 °C
• 沸点：
  442.7±45.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-羟基-8,8-二甲基-9,10-二氢-2H,8H-吡喃并[2,3-f]苯并吡喃-2-酮 在 盐酸 、 3 A molecular sieve 、 mercury dibromide 、 mercury(II) oxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.67h， 生成 jatamansinol
  参考文献：
  名称：

  Skaltsounis, Alexios-Leandros; Mitaku, Sofia; Gaudel, Gilbert, Heterocycles, 1992, vol. 34, # 1, p. 121 - 128

  摘要：

  DOI：
• 作为产物：
  描述：

  奥斯生诺 在 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 15.0h， 以79%的产率得到9-羟基-8,8-二甲基-9,10-二氢-2H,8H-吡喃并[2,3-f]苯并吡喃-2-酮
  参考文献：
  名称：

  香豆素衍生物的合成及其对t -BHP诱导的HepG2细胞氧化损伤的细胞保护作用

  摘要：

  香豆素普遍存在于高等植物中，并表现出各种生物学作用。这项研究的目的是调查香豆素衍生物对叔丁基过氧化氢（t -BHP）诱导的人肝癌HepG2细胞氧化损伤的构效关系。制备了一系列香豆素衍生物，并对其细胞保护作用进行了评估。其中，与咖啡酸结合的二氢吡喃香豆素衍生物，咖啡酰洛美汀可有效地保护免受t- BHP引起的细胞损伤。我们的研究结果表明，咖啡酰lomatin似乎是一种有效的细胞保护剂。

  DOI：

  10.1016/j.bmcl.2018.06.018

文献信息

• Structure–activity relationships for naturally occurring coumarins as β-secretase inhibitor
  作者：Shinsuke Marumoto、Mitsuo Miyazawa

  DOI：10.1016/j.bmc.2011.12.002

  日期：2012.1

  The present study was demonstrated to evaluate the effects of naturally occurring coumarins (NOCs) including simple coumarins, furanocoumarins, and pyranocoumarins on the inhibition of β-secretase (BACE1) activity. Of 41 NOCs examined, some furanocoumarins inhibited BACE1 activity, but simple coumarins and pyranocoumarins did not affect. The most potent inhibitor was 5-geranyloxy-8-methoxypsoralen

  本研究证明可以评估天然香豆素（NOC）（包括简单香豆素，呋喃香豆素和吡喃香豆素）对β-分泌酶（BACE1）活性的抑制作用。在41个NOC中，一些呋喃香豆素抑制了BACE1的活性，但简单的香豆素和吡喃香豆素没有影响。最有效的抑制剂是5-香叶基氧基-8-甲氧基补骨脂素（31），IC 50值为9.9μM 。其他呋喃香豆素衍生物，例如8-香叶基氧基-5-甲氧基补骨脂素（35），8-香叶基氧基补骨脂蛋白（24）和佛手柑（18）抑制BACE1活性，IC 50值<25.0μM。通过狄克逊曲线和Cornish-鲍登地块抑制机制的分析表明，化合物18，31和35混合型抑制剂。香豆素24抑制BACE1的动力学是非竞争性抑制剂。
• COMPOUNDS, COMPOSITIONS AND METHODS FOR PREVENTING SKIN DARKENING
  申请人：Orlow Seth J.

  公开号：US20110190229A1

  公开（公告）日：2011-08-04

  A method for preventing hyperpigmented skin, undesired pigmentation disorder of skin, or undesired darkening of skin using coumarin compounds, the use of such compounds, and compositions and formulations thereof are disclosed. In a particular embodiment, the coumarin compounds are selected from robustic acid methyl ether, scandenin, and coumophos. The compounds may be prepared as additives to pharmaceutical and cosmetic compositions, and in personal care products such as antiperspirants. In a particular embodiment extends to an antiperspirant product containing a skin darkening inhibitory amount of a compound of the invention. Also, the present skin darkening compounds may be prepared in combination with each other. The compounds, compositions and formulations of the invention may be used for the prevention of the onset or progression of conditions characterized by unwanted skin darkening, including those that may be causally related to aberrant melanogenesis activity including, by way of non-limiting example, hyperpigmentation and others.
• COUMARIN COMPOUNDS AS MELANOGENESIS MODIFIERS AND USES THEREOF
  申请人：ORLOW Seth J.

  公开号：US20120220545A1

  公开（公告）日：2012-08-30

  Provided are coumarin compounds of formula I, for example, robustic acid methyl ether, and the use of such compounds and compositions thereof to modulate (e.g., inhibit) melanogenesis and pigmentation. wherein R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are described herein. Also provided are plant extracts containing a compound of formula I, and the use of such a plant extract to modulate (e.g., inhibit) melanogenesis and pigmentation. The compound or plant extract may be prepared as pharmaceutical and cosmetic compositions, and may be used for the prevention and treatment of conditions that are related to aberrant melanogenesis activity.
• US8563754B2
  申请人：——

  公开号：US8563754B2

  公开（公告）日：2013-10-22
• US8772252B2
  申请人：——

  公开号：US8772252B2

  公开（公告）日：2014-07-08