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7-(benzyloxy)-5-hydroxy-2-phenyl-4H-chromen-4-one | 110506-85-9

中文名称
——
中文别名
——
英文名称
7-(benzyloxy)-5-hydroxy-2-phenyl-4H-chromen-4-one
英文别名
5-hydroxy-7-benzyloxyflavone;5-hydroxy-2-phenyl-7-phenylmethoxychromen-4-one
7-(benzyloxy)-5-hydroxy-2-phenyl-4H-chromen-4-one化学式
CAS
110506-85-9
化学式
C22H16O4
mdl
——
分子量
344.367
InChiKey
HIYMWHBMOOSAEF-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.9
  • 重原子数:
    26
  • 可旋转键数:
    4
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.05
  • 拓扑面积:
    55.8
  • 氢给体数:
    1
  • 氢受体数:
    4

SDS

SDS:43726e0895062cb82f4542e72a8e0ae1
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上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
    • 1
    • 2

反应信息

  • 作为反应物:
    描述:
    7-(benzyloxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 在 palladium on activated charcoal 甲酸 、 sodium formate 作用下, 以 甲醇 为溶剂, 反应 2.0h, 以90%的产率得到白杨素
    参考文献:
    名称:
    Krishnamurty, H. G.; Ghosh, Sanjukta; Sathyanarayana, S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 1253 - 1254
    摘要:
    DOI:
  • 作为产物:
    参考文献:
    名称:
    槲皮素3-葡萄糖苷的同位素标记
    摘要:
    潜在重要的饮食抗氧化剂槲皮素3 - O -β-d-葡萄糖苷已通过从[ 13 C]二氧化碳经过5步合成,以15%的产率在类黄酮单元的C-2处被13 C标记。该路线适用于放射化学合成。受保护的3-葡萄糖基化黄酮醇的形成似乎是由[1,7]-σ重排导致的,其中苄基迁移,然后环化。即使使用磷腈超强碱,也会产生游离的5-OH。
    DOI:
    10.1016/j.tet.2006.05.046
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文献信息

  • 신규 화합물 및 이를 유효성분으로 함유하는 섬유증 또는 비알코올성 지방간염의 예방, 개선 또는 치료용 조성물
    申请人:OsteoNeuroGen (주)오스티오뉴로젠(120130541777) Corp. No ▼ 131111-0353919BRN ▼144-81-18250
    公开号:KR101871166B1
    公开(公告)日:2018-07-02
    본 발명은 신규 화합물 및 이를 유효성분으로 함유하는 섬유증 또는 비알코올성 지방간염의 예방, 개선 또는 치료용 조성물에 관한 것으로, 구체적으로 섬유증의 예방, 개선 또는 치료 효과가 우수한 화학식 1의 신규 화합물 및 이를 유효성분으로 함유하는 섬유증 또는 비알코올성 지방간염의 예방, 개선 또는 치료용 조성물에 관한 것이다. 본 발명의 신규 화합물은 EMT(Epithelial Mesenchymal Transition, 상피간엽이행)의 조절인자인 snail 및 vimentin의 발현을 효과적으로 조절하여 EMT의 활성화를 조절하고, 이에 따라 섬유증을 효과적으로 예방, 개선 또는 치료할 수 있다. 뿐만 아니라 본 발명의 신규 화합물은 약물동력학적 특성도 매우 우수하여 구강투여로도 체내에 빠른 약물전달이 가능하고, 체내에서 안정적인 효과를 발휘할 수 있으며, 큰 부작용이 없어 안전하게 사용할 수 있다. 또한 본 발명의 신규 화합물은 간세포의 섬유화를 효과적으로 차단할 수 있어 비알코올성 지방간염도 효과적으로 개선 또는 치료할 수 있다.
    本发明涉及一种新化合物及其在纤维症或非酒精性脂肪肝的预防、改善或治疗组合物中的有效成分,具体涉及一种新化合物化学式1,其具有优越的纤维症预防、改善或治疗效果,并将其作为有效成分用于纤维症或非酒精性脂肪肝的预防、改善或治疗组合物。该新化合物通过有效调节上皮间质转化(EMT)调节因子snail和vimentin的表达,从而有效调节EMT的活化,进而可以有效预防、改善或治疗纤维症。此外,该新化合物的药代动力学特性也非常优越,可以通过口服快速传递到体内,并在体内产生稳定的效果,没有明显的副作用,可以安全使用。此外,该新化合物还可以有效阻止肝细胞的纤维化,从而也可以有效改善或治疗非酒精性脂肪肝。
  • USE OF CHROMONE DERIVATIVE AS PHARMACEUTICAL COMPOSITION FOR PREVENTION AND TREATMENT OF FIBROSIS USING EMT INHIBITORY ACTIVITY
    申请人:OSTEONEUROGEN INC.
    公开号:US20170239211A1
    公开(公告)日:2017-08-24
    A pharmaceutical composition contains the chromone derivative of Chemical Formula 1 and a pharmaceutically acceptable salt as an active ingredient, thus effectively inhibiting the activation of EMT to thereby enable the effective suppression of a disease caused by fibrosis of an organ or tissue in vivo due to the activation of EMT.
    一种药物组合物包含化学式1的咖啡酮衍生物和一种药用可接受的盐作为活性成分,从而有效抑制EMT的激活,从而使得能够有效抑制由于EMT激活而导致的器官或组织纤维化引起的疾病。
  • Synthetic Silvestrol Analogues as Potent and Selective Protein Synthesis Inhibitors
    作者:Tao Liu、Somarajan J. Nair、André Lescarbeau、Jitendra Belani、Stéphane Peluso、James Conley、Bonnie Tillotson、Patrick O’Hearn、Sherri Smith、Kelly Slocum、Kip West、Joseph Helble、Mark Douglas、Adilah Bahadoor、Janid Ali、Karen McGovern、Christian Fritz、Vito J. Palombella、Andrew Wylie、Alfredo C. Castro、Martin R. Tremblay
    DOI:10.1021/jm3011542
    日期:2012.10.25
    intermediates of silvestrol and explore structure–activity relationships around the C6 position. The ability of silvestrol and analogues to selectively inhibit the translation of proteins with high requirement on the translation–initiation machinery (i.e., complex 5′-untranslated region UTR) relative to simple 5′UTR was determined by a cellular reporter assay. Simplified analogues of silvestrol such as compounds
    蛋白质翻译失调在人类癌症发病机理的许多层面上都起着至关重要的作用。西尔维斯托尔,环戊达[ b]苯并呋喃天然产物通过干扰eIF4F翻译复合物的组装,在起始步骤阻止翻译。Silvestrol具有复杂的化学结构,其官能团的要求尚未得到系统的研究。而且,由于药物样性质差,silvestrol具有有限的发展潜力。在本文中,我们寻求开发Silvestrol关键中间体的实用合成方法,并探索C6位置周围的构效关系。相对于简单的5'UTR,silvestrol和类似物选择性抑制蛋白质翻译的能力(相对于简单的5'UTR,对翻译起始机制(即复杂的5'-非翻译区UTR)有很高的要求)。Silvestrol的简化类似物,例如化合物74与silvestrol相比,它们中的76种和76种具有相似的细胞毒性作用和更好的ADME特性。
  • [EN] COMPOUNDS AND METHODS TO INCREASE ANTI-P-GLYCOPROTEIN ACTIVITY OF BAICALEIN BY ALKYLATION ON THE A RING<br/>[FR] COMPOSES ET METHODES DESTINEES A AUGMENTER L'ACTIVITE ANTI-GLYCOPROTEINE P PAR ALKYLATION SUR LE NOYAU A
    申请人:UNIV YALE
    公开号:WO2005075449A1
    公开(公告)日:2005-08-18
    The present invention is directed to analogs of baicalein according to formula (I): where R5 is H, (CI-C12)alkyl, (C2-C13)acyl, or an optionally substituted phenyl or benzyl group, an acyl group, a C1-C20 alkyl or ether group, a phosphate, diphosphate, triphosphate or phosphodiester group; R6 and R7 are each independently H, (C1-C12)alkyl, (C2-C13)acyl, or an optionally substituted phenyl or benzyl or together form a -OCR1R20- group wherein each of R1 and R2 is independently H, a C1-C3 alkyl group or an optionally substituted phenyl or benzyl group; and R8 is H, OH, an O-acyl group, a C1,-C4 alkyl or alkoxy group, F, Cl, Br or I, or a pharmaceutically acceptable salt thereof, which exhibit anti-P-glycoprotein activity and methods of enhancing the bioavailability of active compounds, especially orally administered compounds, by inhibition of P-glycoprotein 170 (P-gp 170) and/or CYP450 enzyme, especially CYP450 3A4 enzyme. Pharmaceutical compositions based upon these novel derivatives according to the present invention are also described herein.
    本发明涉及根据式(I)的黄芩素类似物:其中R5为H,(C1-C12)烷基,(C2-C13)酰基,或者一个可选择取代的苯基或苄基团,酰基,C1-C20烷基或醚基,磷酸酯,二磷酸酯三磷酸酯磷酸二酯基团;R6和R7各自独立地为H,(C1-C12)烷基,(C2-C13)酰基,或者一个可选择取代的苯基或苄基,或者一起形成一个-OCR1R20-基团,其中R1和R2中的每一个独立地为H,C1-C3烷基或可选择取代的苯基或苄基团;以及R8为H,OH,一个O-酰基团,一个C1-C4烷基或烷氧基团,F,Cl,Br或I,或其药学上可接受的盐,具有抗P-糖蛋白活性,并通过抑制P-糖蛋白170 (P-gp 170)和/或CYP450酶,特别是CYP450 3A4酶,来增强活性化合物的生物利用度的方法。根据本发明的这些新颖衍生物基础上的药物组合物也在此描述。
  • Synthesis and inhibition of PGE production of 6,8-disubstituted chrysin derivatives
    作者:H PARK、T DAO、H KIM
    DOI:10.1016/j.ejmech.2005.04.013
    日期:2005.9
    A series of 6,8-disubstituted chrysin derivatives have been synthesized and evaluated for their PGE2 inhibitory activities. 6,8-Disubstituted chrysin derivatives were obtained from naturally occurring chrysin by halogenation, oxidation, thiomethylation and C-C cross coupling reaction. Among the compounds investigated, 6,8-dibromochrysin (2), 6,8-diiodochrysin (4), 6,8-dimethylthiochrysin (9) and 6
    已经合成了一系列的6,8-二取代的chrysin衍生物,并评估了其对PGE2的抑制活性。通过卤化,氧化,代甲基化和CC交叉偶联反应从天然存在的菊花素中获得6,8-二取代的菊花素衍生物。在所研究的化合物中,6,8-二代菊花链(2),6,8-二代菊花链(4),6,8-二甲基硫代菊花链(9)和6,8-二甲氧基菊花链(11)具有很强的抑制LPS产生PGE2的活性。诱导的RAW 264.7细胞为wogonin,这是一种众所周知的天然黄酮,具有很强的选择性COX-2抑制活性。
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