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benzyl glycyrrhetate | 51984-75-9

中文名称
——
中文别名
——
英文名称
benzyl glycyrrhetate
英文别名
benzyl (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylate;Benzyl (20beta)-3beta-hydroxy-12-oxoolean-12-en-29-oate;benzyl (2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylate
benzyl glycyrrhetate化学式
CAS
51984-75-9
化学式
C37H52O4
mdl
——
分子量
560.817
InChiKey
UNRVOFRDIGTQBY-CJBAOGIUSA-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):
    8.2
  • 重原子数:
    41
  • 可旋转键数:
    4
  • 环数:
    6.0
  • sp3杂化的碳原子比例:
    0.73
  • 拓扑面积:
    63.6
  • 氢给体数:
    1
  • 氢受体数:
    4

SDS

SDS:2b155c3ed7ccfc5cd462bbf574aff045
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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

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文献信息

  • Synthesis and biological activity of glycyrrhetinic acid derivatives as antitumor agents
    作者:Fei Zhou、Gao-Rong Wu、De-Sheng Cai、Bing Xu、Meng-Meng Yan、Tao Ma、Wen-Bo Guo、Wen-Xi Zhang、Xue-Mei Huang、Xiao-hui Jia、Yu-Qin Yang、Feng Gao、Peng-Long Wang、Hai-Min Lei
    DOI:10.1016/j.ejmech.2019.06.029
    日期:2019.9
    all the de-protected (without Boc group) derivatives showed much stronger cytotoxic activity than GA, and surprisingly enough, all the GN series of the compounds were more potent than GO series against various tumor cells. Among them, the compound 26 (amide linkages in C-3 position) exhibited stronger antitumor activity against A549 cell line (IC50 = 2.109 ± 0.11 μM) than the positive drug cisplatin (IC50 = 9
    甘草次酸(GA)一直是抗癌的先导化合物,并吸引了世界各地的许多科学家。然而,其抗肿瘤活性还不够强。为提高GA的细胞毒性并探讨键合方式对抗肿瘤活性的影响,GA-OH系列(GO,C-3位的酯)和GA-NH 2系列(GN,C-3位的酰胺键)包括32种化合物已经被设计和合成了。对所有化合物进行了体外筛选对A549,HepG2,MCF-7,Hela和MDCK细胞系的细胞毒性。结果,所有去保护的(没有Boc基团)衍生物都显示出比GA强得多的细胞毒活性,而且令人惊讶的是,所有GN系列化合物对各种肿瘤细胞的功效都比GO系列更强。其中,化合物26(位于C-3位置的酰胺键)对A549细胞系(IC 50  = 2.109±0.11μM )表现出比阳性药物顺铂(IC 50  = 9.001±0.37μM)更强的抗肿瘤活性。进一步的研究表明,化合物26可以通过细胞核断裂诱导A549细胞凋亡。凋亡的检测和细胞周期分析
  • 2,4-Dinitrobenzenesulfonamide-Directed S<sub>N</sub>2-Type Displacement Reaction Enables Synthesis of β-<scp>d</scp>-Glycosaminosides
    作者:Xianyang Wang、Peng Wang、Dongwei Li、Ming Li
    DOI:10.1021/acs.orglett.9b00688
    日期:2019.4.5
    l linkages was established using nonparticipating and strong electron-withdrawing C-2-2,4-dinitrobenzenesulfonamide (DNsNH)-directed SN2-like glycosylation of glycosyl ortho-hexynylbenzoates. The reaction is applicable to a wide range of O-, N-, and C-nucleophiles and features convenient conversion of DNsNH into AcNH in high yield under mild conditions. Oligomerization-ready trisaccharide, composed
    使用不参与和强吸电子的C-2-2,4-二硝基苯磺酰胺(DNsNH)定向的糖基邻己基苯甲酸酯的S N 2样糖基化,建立了构建β- d-葡萄糖-/半乳糖基基连接的有效方案。该反应适用于各种O-,N-和C-亲核试剂,并且具有在温和条件下将DNsNH方便地高产率转化为AcNH的特征。由β- d-(1→3)-葡糖基残基组成的易于寡聚的三糖已获得,为合成与脑膜炎奈瑟氏球菌荚膜多糖相关的寡糖奠定了坚实的基础。
  • Synthesis and antitumour activity of glycyrrhetinic acid derivatives
    作者:Stefan Schwarz、René Csuk
    DOI:10.1016/j.bmc.2010.08.054
    日期:2010.11
    Glycyrrhetinic acid (GA) is one of many interesting triterpenoic acids showing anticancerogenic potential. GA is known to trigger apoptosis in tumour cell lines, although GA has a low cytotoxicity. In our study we were able to prepare derivatives of GA that show lowered the IC50 values as determined by a sulforhodamine B (SRB) assay using 15 different human tumour cell lines. Thus, combining an ester
    甘草次酸(GA)是显示出抗癌潜力的许多有趣的三萜酸之一。尽管GA具有低细胞毒性,但是已知GA可以触发肿瘤细胞系的凋亡。在我们的研究中,我们能够制备GA衍生物,该衍生物显示出通过使用15种不同的人类肿瘤细胞系的磺基罗丹明B(SRB)分析确定的IC 50值降低。因此,结合酯基结合氨基酸部分的存在导致ca。抗肿瘤活性提高60倍。在小鼠胚胎成纤维细胞(NiH3T3)上进行的实验表明,与母体化合物GA相比,这些化合物对肿瘤细胞表现出更好的选择性。使用an啶橙/化乙锭(AO / EB)测试和DNA阶梯实验确定了其中某些化合物的凋亡作用。
  • [EN] GLYCYRRHETINIC ACID DERIVATIVES FOR TREATING HYPERKALEMIA<br/>[FR] DÉRIVÉS D'ACIDE GLYCYRRHÉTINIQUE DE TRAITEMENT DE L'HYPERKALIÉMIE
    申请人:ARDELYX INC
    公开号:WO2019060051A1
    公开(公告)日:2019-03-28
    The present invention provides a compound of formula (I) or a salt thereof: (I) wherein X, L, V, R1, R2, R3 and R4, are as defined herein. These compounds are inhibitors of 11-hydroxysteroid dehydrogenase type 2 (11-HSD-2) and are used to treat hyperkalemia.
    本发明提供了化合物(I)或其盐:(I)其中X、L、V、R1、R2、R3和R4如本文所定义。这些化合物是11-羟基类固醇脱氢酶2型(11-HSD-2)的抑制剂,用于治疗高血症。
  • Studies on the enzyme immunoassay of bio-active constituents contained in oriental medicinal drugs. IV. Enzyme immunoassay of glycyrrhetic acid.
    作者:MATAO KANAOKA、SABURO YANO、HIROMI KATO、TAKAKO NAKADA、KAZUHIRO KAWAMURA
    DOI:10.1248/cpb.36.8
    日期:——
    Enzyme immunoassay of glycyrrhetic acid was developed by employing antisera elicited from in rabbits immunized with C-3 bridged glycyrrhetic acid-bovine serum albumin (BSA) conjugate (15, 16) and C-3 bridged glycyrrhetic acid-β-galactosidase conjugate (17, 18) as labeled antigens. Hemisuccinyl and hemiglutaryl groups, which were chosen as the chemical bridges, were introduced at the hydroxy group of tert-butyl glycyrrhetate (2). Immunoassay was performed with bridge heterologous combinations such as anti-glycyrrhetic acid-hemisuccinate-BSA (15) antiserum and glycyrrhetic acid-hemiglutarate-β-galactosidase conjugate (18) and the reverse combination (16 and 17). The sensitivity of enzyme immunoassays (EIA) expressed as the midpoint (logit B/B0=0) was higher in the former combination (2.4 ng/tube) than the reverse combination (8.6 ng/tube). The cross reactivities of the anti-C-3 bridged glycyrrhetic acid antisera with C-3 substituted derivatives of glycyrrhetic acid were higher than those of the anti-C-30 bridged glycyrrhetic acid antiserum.
    利用由C-3桥联甘草次酸-牛血清白蛋白(BSA)偶联物(15, 16)和C-3桥联甘草次酸-β-半乳糖苷酶偶联物(17, 18)作为标记抗原,激发产生的兔抗血清,开发了甘草次酸的酶免疫分析方法。选择了半琥珀酰和半谷酰基团作为化学桥联,引入到叔丁基甘草次酸的羟基上(2)。通过桥联异源组合,如抗甘草次酸-半琥珀酸-BSA(15)抗血清和甘草次酸-半谷酸盐-β-半乳糖苷酶偶联物(18)以及反向组合(16和17)进行免疫测定。酶免疫分析(EIA)的灵敏度,以中点(logit B/B0=0)表示,在前一种组合(2.4 ng/管)中高于反向组合(8.6 ng/管)。抗C-3桥联甘草次酸抗血清与C-3取代的甘草次酸生物的交叉反应性高于抗C-30桥联甘草次酸抗血清。
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同类化合物

(5β,6α,8α,10α,13α)-6-羟基-15-氧代黄-9(11),16-二烯-18-油酸 (3S,3aR,8aR)-3,8a-二羟基-5-异丙基-3,8-二甲基-2,3,3a,4,5,8a-六氢-1H-天青-6-酮 (2Z)-2-(羟甲基)丁-2-烯酸乙酯 (2S,4aR,6aR,7R,9S,10aS,10bR)-甲基9-(苯甲酰氧基)-2-(呋喃-3-基)-十二烷基-6a,10b-二甲基-4,10-dioxo-1H-苯并[f]异亚甲基-7-羧酸盐 (1aR,4E,7aS,8R,10aS,10bS)-8-[((二甲基氨基)甲基]-2,3,6,7,7a,8,10a,10b-八氢-1a,5-二甲基-氧杂壬酸[9,10]环癸[1,2-b]呋喃-9(1aH)-酮 (+)顺式,反式-脱落酸-d6 龙舌兰皂苷乙酯 龙脑香醇酮 龙脑烯醛 龙脑7-O-[Β-D-呋喃芹菜糖基-(1→6)]-Β-D-吡喃葡萄糖苷 龙牙楤木皂甙VII 龙吉甙元 齿孔醇 齐墩果醛 齐墩果酸苄酯 齐墩果酸甲酯 齐墩果酸溴乙酯 齐墩果酸二甲胺基乙酯 齐墩果酸乙酯 齐墩果酸3-O-alpha-L-吡喃鼠李糖基(1-3)-beta-D-吡喃木糖基(1-3)-alpha-L-吡喃鼠李糖基(1-2)-alpha-L-阿拉伯糖吡喃糖苷 齐墩果酸 beta-D-葡萄糖酯 齐墩果酸 beta-D-吡喃葡萄糖基酯 齐墩果酸 3-乙酸酯 齐墩果酸 3-O-beta-D-葡吡喃糖基 (1→2)-alpha-L-吡喃阿拉伯糖苷 齐墩果酸 齐墩果-12-烯-3b,6b-二醇 齐墩果-12-烯-3,24-二醇 齐墩果-12-烯-3,21,23-三醇,(3b,4b,21a)-(9CI) 齐墩果-12-烯-3,21,23-三醇,(3b,4b,21a)-(9CI) 齐墩果-12-烯-3,11-二酮 齐墩果-12-烯-2α,3β,28-三醇 齐墩果-12-烯-29-酸,3,22-二羟基-11-羰基-,g-内酯,(3b,20b,22b)- 齐墩果-12-烯-28-酸,3-[(6-脱氧-4-O-b-D-吡喃木糖基-a-L-吡喃鼠李糖基)氧代]-,(3b)-(9CI) 齐墩果-12-烯-28-酸,3,7-二羰基-(9CI) 齐墩果-12-烯-28-酸,3,21,29-三羟基-,g-内酯,(3b,20b,21b)-(9CI) 鼠特灵 鼠尾草酸醌 鼠尾草酸 鼠尾草酚酮 鼠尾草苦内脂 黑蚁素 黑蔓醇酯B 黑蔓醇酯A 黑蔓酮酯D 黑海常春藤皂苷A1 黑檀醇 黑果茜草萜 B 黑五味子酸 黏黴酮 黏帚霉酸