3-(7S)-(+)-8,8-dimethyl-7-(3-phenylallyloxy)-7,8-dihydro-6H-pyrano[3,2-g]chromen-2-one | 2249696-72-6

• 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: 3-(7S)-(+)-8,8-dimethyl-7-(3-phenylallyloxy)-7,8-dihydro-6H-pyrano[3,2-g]chromen-2-one
• 英文别名: (7S)-(+)-(E)-8,8-dimethyl-7-(3-phenylallyloxy)-7,8-dihydro-6H-pyrano[3,2-g]chromen-2-one；(7S)-(+)-8,8-dimethyl-7-(3-phenylallyloxy)-7,8-dihydro-6H-pyrano[3,2-g]chromen-2-one；(S,E)-(+)-8,8-dimethyl-7-(3-phenylallyloxy)-6,7-dihydro-2H,8H-pyrano[3,2-g]chromen-2-one；426P9Hsr8I；(3S)-2,2-dimethyl-3-[(E)-3-phenylprop-2-enoxy]-3,4-dihydropyrano[3,2-g]chromen-8-one
• CAS: 2249696-72-6
• 化学式: C₂₃H₂₂O₄
• 分子量: 362.425
• InChiKey: KTTIANPTCWGYCN-JLXBBBJOSA-N

物化性质

• 沸点：
  551.4±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-苯基丙-2-烯-1-醇 在 三溴化磷 、 sodium hydride 、 sodium sulfate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3-(7S)-(+)-8,8-dimethyl-7-(3-phenylallyloxy)-7,8-dihydro-6H-pyrano[3,2-g]chromen-2-one
  参考文献：
  名称：

  PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING AGING-RELATED DISEASES CONTAINING DECURSIN DERIVATIVE AS ACTIVE INGREDIENT

  摘要：

  一种用于预防或治疗与衰老相关疾病的组合物包括一种新的脱氧雪莲素衍生物作为活性成分，其中该新的脱氧雪莲素衍生物已经表现出抑制晚年蛋白表达和抑制晚年蛋白与 lamin A 结合的优异效果，并已确认该新的脱氧雪莲素衍生物延长了诱导晚年蛋白的动物模型的存活期。

  公开号：

  US20200048274A1

文献信息

• Suppressive activities of KC1–3 on HMGB1-mediated septic responses
  作者：Wonhwa Lee、O. Yuseok、Changhun Lee、So Yeon Jeong、Jee-Hyun Lee、Moon-Chang Baek、Gyu-Yong Song、Jong-Sup Bae

  DOI：10.1016/j.bcp.2019.02.027

  日期：2019.5

  anti-septic activities on high mobility group box 1 (HMGB1)-mediated septic responses and survival rate in a mouse model of sepsis. KC1 and KC3, but not KC2, significantly reduced HMGB1 release in lipopolysaccharide (LPS)-activated human umbilical vein endothelial cells (HUVECs) and attenuated the cecal ligation and puncture (CLP)-induced release of HMGB1. Additionally, in vitro analyses revealed that KC1

  在本研究中，合成了几种decursin类似物（KC1-3），并根据其对败血症小鼠模型中对高迁移率族1（HMGB1）介导的败血反应的防腐活性和存活率进行了评估。KC1和KC3，而不是KC2，显着降低了脂多糖（LPS）激活的人脐静脉内皮细胞（HUVEC）中的HMGB1释放，并减弱了盲肠结扎和穿刺（CLP）诱导的HMGB1释放。此外，体外分析显示，KC1和KC3均减轻了HMGB1介导的血管破坏并抑制了小鼠的通透性，而体内分析显示，KC1和KC3降低了败血症相关的死亡率和组织损伤。综上所述，目前的结果表明，KC1和KC3均可降低HMGB1的释放和败血病的死亡率，因此，
• Pharmaceutical composition for preventing or treating aging-related diseases containing decursin derivative as active ingredient
  申请人：PRG S&TECH INC.

  公开号：US11008332B2

  公开（公告）日：2021-05-18

  A composition for preventing or treating an aging-related disease includes a novel decursin derivative as an active ingredient, wherein the novel decursin derivative has exhibited an excellent effect of inhibiting progerin expression and excellent effect of inhibiting binding between progerin and lamin A, and it has been confirmed that the novel decursin derivative prolongs the survival period of animal models in which progerin was induced.

  一种用于预防或治疗衰老相关疾病的组合物包括一种新型脱壳素衍生物作为活性成分，其中该新型脱壳素衍生物在抑制早老素表达方面具有极佳的效果，在抑制早老素与层粘连蛋白 A 之间的结合方面也具有极佳的效果，并且已证实该新型脱壳素衍生物可延长诱导早老素的动物模型的存活期。
• 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.
• [EN] NOVEL METHOD FOR SYNTHESIZING DECURSIN DERIVATIVE<br/>[FR] NOUVEAU PROCÉDÉ DE SYNTHÈSE D'UN DÉRIVÉ DE DÉCURSINE<br/>[KO] 데커신 유도체의 신규 합성방법
  申请人：PRG S&TECH INC

  公开号：WO2021132872A1

  公开（公告）日：2021-07-01

  본 발명은 데커신 유도체의 신규 합성방법에 관한 것으로, (Ⅰ) 신나밀 브로마이드(Cinnamyl bromide)와 N-메틸-2-피로리돈[N-Methyl-2-pyrrolidone; NMP] 용매를 혼합하여 용액을 제조하는 단계; (Ⅱ) 데커시놀(Decursinol)과 테트라히드로푸란(Tetrahydrofuran;THF) 용매 및 소듐 하이드라이드(Sodium hydride; NaH)를 혼합하여 용액을 제조하는 단계; 및 (Ⅲ) 상기 (Ⅰ) 및 (Ⅱ) 단계에서 제조된 용액을 혼합하여 데커신 유도체를 수득하는 단계; 를 포함하여 수득되는 데커신 유도체 화합물의 수율을 높일 수 있으며, 대량생산이 가능하다.
• NOVEL METHOD FOR SYNTHESIZING DECURSIN DERIVATIVE
  申请人：PRG S&TECH INC.

  公开号：US20230063754A1

  公开（公告）日：2023-03-02

  The present invention relates to a novel method for synthesizing a decursin derivative, the method comprising: a step (I) for preparing a solution by mixing cinnamyl bromide and an N-Methyl-2-pyrrolidone [N-Methyl-2-pyrrolidone (NMP)] solvent; a step (II) for preparing a solution by mixing decursinol, a tetrahydrofuran (THF) solvent, and sodium hydride (NaH); and a step (III) for obtaining a decursin derivative by mixing the solutions prepared in step (I) and step (II). The method can increase the yield of the obtained decursin derivative compound and enables mass production.