smyrinol monoacetate | 23027-51-2

• 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: smyrinol monoacetate
• 英文别名: (7S)-(+)-acetic acid 8,8-dimethyl-2-oxo-6,7-dihydro-2H,8H-pyrano[3,2-g]chromen-7-yl ester；acetic acid (S)-2,2-dimethyl-8-oxo-3,4-dihydro-2H,8H-pyrano[3,2-g]-chromen-3-yl-ester；acetic acid 2,2-dimethyl-8-oxo-3,4-dihydro-2H,8H-pyrano[3,2-g]chromen-3-yl ester；[(3S)-2,2-dimethyl-8-oxo-3,4-dihydropyrano[3,2-g]chromen-3-yl] acetate
• CAS: 23027-51-2
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: KPVAGSQSZBIVAD-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  日本前胡醇 、 乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以89.8%的产率得到smyrinol monoacetate
  参考文献：
  名称：

  Synthesis of (S)-(+)-decursin and its analogues as potent inhibitors of melanin formation in B16 murine melanoma cells

  摘要：

  We report the synthesis of a novel series of highly potent melanin inhibitors which were obtained through structural modification of an anticancer compound S-(+)-decursinol. The in vitro inhibitory potencies of the newly synthesized compounds were evaluated against alpha-MSH induced melanin production in 816 murine melanoma cells. Among the compounds evaluated, compounds 2, 3, 6b, 7a, 7b, 8a and 8b emerged as highly potent inhibitors of melanin production. Besides, these compounds demonstrated significantly low cytotoxicity. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.006

文献信息

• Coumarins of Smyrniopsis aucheri
  作者：Z. R. Dzhafarov、Z. A. Kuliev、A. D. Vdovin、A. A. Kuliev、V. M. Malikov、N. M. Ismailov

  DOI：10.1007/bf00629787

  日期：——
• [EN] NOVEL DECURSIN DERIVATIVES AND THE USE THEREOF<br/>[FR] NOUVEAUX DÉRIVÉS DE LA DÉCURSINE ET LEUR UTILISATION
  申请人：PARK YONG JIN

  公开号：WO2008004817A1

  公开（公告）日：2008-01-10

  [EN] The present invention relates to novel (+)-decursin derivatives having anti-cancer activity, the preparation thereof and a composition containing the same for treating cancer disease. The (+)-decursin derivatives of the present invention showed potent inhibiting effect on the cancer cell being confirmed by various experiments such as cytotoxicity test in A549 lung cancer cell line, HCT15 colon cancer cell line and ACHN rectal cancer cell line, therefore the compounds can be useful in treating or preventing cancer diseases as an anti-cancer agent, health care food, or functional health food.
  [FR] L'invention concerne de nouveaux dérivés de la (+)-décursine ayant une activité anti-cancéreuse, leur préparation et une composition les renfermant pour le traitement du cancer. Les dérivés de la (+)-décursine selon l'invention possèdent un puissant effet inhibiteur sur les cellules cancéreuses, comme le confirment divers essais tels que le test de cytotoxicité dans la lignée cellulaire du cancer du poumon A549, la lignée cellulaire du cancer du colon HCT15 et la lignée cellulaire du cancer rectal ACHN, de sorte que les composés peuvent être utilisés dans le traitement ou la prévention des maladies cancéreuses en tant qu'agents anticancéreux, aliments diététiques ou aliments diététiques fonctionnels.
• Synthesis of (S)-(+)-decursin and its analogues as potent inhibitors of melanin formation in B16 murine melanoma cells
  作者：Kyeong Lee、Jee-Hyun Lee、Shanthaveerappa K. Boovanahalli、Yongseok Choi、Soo-Jin Choo、Ick-dong Yoo、Dong Hee Kim、Mi Young Yun、Gye Won Lee、Gyu-Yong Song

  DOI：10.1016/j.ejmech.2010.09.006

  日期：2010.12

  We report the synthesis of a novel series of highly potent melanin inhibitors which were obtained through structural modification of an anticancer compound S-(+)-decursinol. The in vitro inhibitory potencies of the newly synthesized compounds were evaluated against alpha-MSH induced melanin production in 816 murine melanoma cells. Among the compounds evaluated, compounds 2, 3, 6b, 7a, 7b, 8a and 8b emerged as highly potent inhibitors of melanin production. Besides, these compounds demonstrated significantly low cytotoxicity. (C) 2010 Elsevier Masson SAS. All rights reserved.