(7R)-7-hydroxy-8,8-dimethyl-8H-pyrano[3,2-g]chromen-2-on | 21860-31-1

• 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: (7R)-7-hydroxy-8,8-dimethyl-8H-pyrano[3,2-g]chromen-2-on
• 英文别名: 3'(R)-hydroxy-3',4'-dihydroxanthyletin；(-)-(3'R)-decursinol；aegelinol；(R)-(-)-decursinol；Decursinol, (-)-；(3R)-3-hydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one
• CAS: 21860-31-1
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: BGXFQDFSVDZUIW-GFCCVEGCSA-N

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：

  2-(2-furyl)ethenyl isocyanate 、 (7R)-7-hydroxy-8,8-dimethyl-8H-pyrano[3,2-g]chromen-2-on 在 4-二甲氨基吡啶 、 三乙胺 作用下， 反应 3.0h， 以80.9%的产率得到(7R)-(-)-2-(furan-2-yl)vinylcarbamic acid-8,8-dimethyl-2-oxo-6,7-dihydro-2H,8H-pyrano[3,2-g]chromen-7-yl-ester
  参考文献：
  名称：

  NEW COMPOUND FOR INHIBITING BINDING BETWEEN DX2 PROTEIN AND P14/ARF PROTEIN, AND PHARMACEUTICAL COMPOSITION FOR TREATING OR PREVENTING CANCER DISEASE CONTAINING SAME AS EFFECTIVE INGREDIENT

  摘要：

  披露了一种新化合物，该化合物抑制了DX2蛋白与p14/ARF蛋白之间的结合，包括该新化合物作为治疗或预防癌症疾病的有效成分的药物组合物，用于提高耐药抗癌药物的抗癌效果的抗癌辅助剂，以及包括AIMP2-DX2蛋白或其片段的组合物，用于诊断肺癌。

  公开号：

  US20170129904A1
• 作为产物：
  描述：

  美洲花椒素 在 sodium hypochlorite 、 disodium hydrogenphosphate 、 (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III) 、 三氟化硼乙醚 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 72.17h， 生成 (7R)-7-hydroxy-8,8-dimethyl-8H-pyrano[3,2-g]chromen-2-on
  参考文献：
  名称：

  两种对映体纯 Decursin 抗癌衍生物的合成、抗增殖活性及分子对接分析

  摘要：

  我们使用从当归（AGN）根中分离出的（ S ）-紫花苷醇，半合成并评估了一系列两种对映体纯的紫花苷衍生物对A549人肺癌细胞的抗增殖活性。所有合成的化合物均表现出对 A549 细胞生长的广谱抑制活性。特别是，与参考化合物 decursin 相比，具有 ( E )-(呋喃-3-基)丙烯酰基的化合物( S )-2d对 A549 癌细胞表现出最有效的活性 (IC 50 : 14.03 µM) (IC 50 : 14.03 µM) 43.55 µM) 及其对映体( R )-2d (IC 50 : 151.59 µM)。 Western blotting 分析表明， ( S )-2d比 decursin 更强烈地抑制 Janus 激酶 1 (JAK1) 和信号转导子和转录激活激活子 3 (STAT3) 的磷酸化，且呈剂量依赖性，同时对 CXCR7 过表达和总表达没有影响。 STAT3 水平。此外， (

  DOI：

  10.1248/cpb.c23-00718

文献信息

• Asymmetric Synthesis of 2-Substituted Dihydrobenzofurans and 3-Hydroxydihydrobenzopyrans through the Enantioselective Epoxidation of O-Silyl-Protected ortho-Allylphenols
  作者：Hang Jiang、Takaya Sugiyama、Akinari Hamajima、Yasumasa Hamada

  DOI：10.1002/adsc.201000505

  日期：2011.1.10

  The Shi‐type epoxidation of O‐tert‐butyldiphenylsilyl (TBDPS) protected o‐allylphenols serves as an efficient strategy to construct the dihydrobenzofurans and dihydrobenzopyrans in up to 97% ee. This methodology led to the enantioselective synthesis of (+)‐marmesin, (−)‐(3′R)‐decursinol, and (+)‐lomatin.

  的施型环氧化ø -叔丁基二苯基硅烷基（TBDPS）保护ø -allylphenols作为有效的策略来构建二氢苯并呋喃和dihydrobenzopyrans在高达97％的ee值。这种方法导致了（+）的对映选择性合成- marmesin，（ - ） - （3' - [R）-decursinol，和（+） - lomatin。
• Antimicrobial and Antioxidant Activities of Coumarins from the Roots of Ferulago campestris (Apiaceae)
  作者：Adriana Basile、Sergio Sorbo、Vivienne Spadaro、Maurizio Bruno、Antonella Maggio、Nicoletta Faraone、Sergio Rosselli

  DOI：10.3390/molecules14030939

  日期：——

  We report the isolation of several coumarins and the stereochemical assessment of some pyranocoumarins, as well as the antibacterial and antioxidant activities of the three most abundant ones (grandivittin, agasyllin and aegelinol benzoate) isolated from the roots of Ferulago campestris collected in Sicily and of the hydrolysis product (aegelinol). Aegelinol and agasyllin showed antibacterial activity against nine ATCC and the same clinically isolated Gram-positive and Gram-negative bacterial strains. At a concentration between 16 and 125 mg/mL both coumarins showed a significant antibacterial effect against both Gram-negative and Gram-positive bacteria. In particular the ATCC strains Staphylococcus aureus, Salmonella thypii, Enterobacter cloacae and Enterobacter earogenes (MIC = 16 and 32 mg/mL for aegelinol and agasyllin, respectively) were the most inhibited. Antibacterial activity was also found against Helicobacter pylori: a dose-dependent inhibition was shown between 5 and 25 mg/mL. The antioxidant activity of the coumarins was evaluated by their effects on human whole blood leukocytes (WB) and on isolated polymorphonucleate (PMN) chemiluminescence (CL), PMA-stimulated and resting.

  我们报告了几种香豆素的分离、一些吡喃香豆素的立体化学评估，以及从西西里岛采集的野扇蕨根部分离出的三种最丰富的香豆素（grandivittin、agasyllin 和 aegelinol benzoate）及其水解产物（egelinol）的抗菌和抗氧化活性。Aegelinol 和 agasyllin 对九种 ATCC 和相同的临床分离革兰氏阳性和革兰氏阴性细菌菌株具有抗菌活性。在 16 至 125 毫克/毫升的浓度范围内，这两种香豆素对革兰氏阴性菌和革兰氏阳性菌都有显著的抗菌效果。尤其是对 ATCC 菌株金黄色葡萄球菌、甲状腺沙门氏菌、泄殖腔肠杆菌和耳肠杆菌（艾格列醇和阿加西林的 MIC 值分别为 16 和 32 mg/mL）的抑制作用最强。此外，还发现了对幽门螺旋杆菌的抗菌活性：5 至 25 毫克/毫升之间的抑制作用呈剂量依赖性。香豆素的抗氧化活性是通过它们对人全血白细胞（WB）和分离的多形核（PMN）化学发光（CL）（PMA 刺激和静息）的影响来评估的。
• Compound for inhibiting binding between DX2 protein and p14/ARF protein, and pharmaceutical composition for treating or preventing cancer disease containing same as effective ingredient
  申请人：PUSAN NATIONAL UNIVERSITY INDUSTRY-UNIVERSITY COOPERATION FOUNDATION

  公开号：US10280178B2

  公开（公告）日：2019-05-07

  Disclosed is a new compound that inhibits binding between a DX2 protein and a p14/ARF protein, a pharmaceutical composition including the new compound as an effective component for treating or preventing a cancer disease, an anticancer adjuvant for improving an anticancer effect of a drug-resistant anticancer drug, and a composition including an AIMP2-DX2 protein or a fragment thereof for diagnosing lung cancer.

  公开了一种抑制 DX2 蛋白和 p14/ARF 蛋白之间结合的新化合物、一种包括新化合物作为有效成分用于治疗或预防癌症疾病的药物组合物、一种用于改善耐药抗癌药物抗癌效果的抗癌辅助剂，以及一种包括 AIMP2-DX2 蛋白或其片段用于诊断肺癌的组合物。
• 신규한 데커신 유도체, 이의 제조방법 및 이의 용도
  申请人：서울대학교산학협력단

  公开号：KR20230055294A

  公开（公告）日：2023-04-25

  본 발명은 신규한 데커신 유도체 및 이의 용도에 관한 것이다. 상기 데커신 유도체는 다양한 곰팡이의 균사체 성장을 억제하는 효과를 나타내어 항진균 용도 및 방제 용도로 활용할 수 있다. 특히, 데커시놀 클로로아크릴레이트(decursinol chloroacrylate)는 푸자리움 옥시스포럼( Fusarium oxysporum ) 및 마그나포르테 오리자에( Magnaporthe oryzae )의 포자 발아 억제에 우수한 효과를 나타내므로, 푸자리움 옥시스포럼( Fusarium oxysporum ) 및 마그나포르테 오리자에( Magnaporthe oryzae )에 대한 항진균제 및 상기 두 균주로부터 발생할 수 있는 식물병의 예방 및 치료를 위한 방제제 개발에 적용할 수 있을 것이다.

  本发明涉及一种新型脱氧雪腐镰刀菌烯醇衍生物及其应用。所述脱氧雪腐镰刀菌烯醇衍生物显示出抑制多种霉菌菌丝生长的效果，可用于抗真菌和防治用途。特别是，脱氧雪腐镰刀菌醇氯乙酰化物（Decursinol chloroacrylate）对Fusarium oxysporum（大丽轮枝菌）和Magnaporthe oryzae（稻瘟病菌）的孢子发芽抑制表现出优异的效果，因此，可用于开发针对这两种真菌的抗真菌剂，以及预防和治疗由它们引起的植物病害。
• Two Dihydropyranocoumarins from Peucedanum wawrii
  作者：Ling-Yi Kong、Xian-Li Wu、Masatake Niwa

  DOI：10.3987/com-02-9629

  日期：——

  Two dihydropyranocoumarins were isolated from the root of Peucedanum wawrii and the structures were established as 3'(R)-acetoxy-3',4'-dihydroxanthyletin (1) and 3'(R)-acetoxy-4'(S)-angeloyloxy-3',4'-dihydroseselin (2), respectively, by spectroscopic methods. The absolute configurations were deduced by chemical correlations with known compounds.