3β,7β-cholest-5-ene-3,7-diol-3-benzoate | 17974-80-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β,7β-cholest-5-ene-3,7-diol-3-benzoate
• 英文别名: 7β-hydroxycholesteryl benzoate；3β-benzoyloxy-cholest-5-en-7β-ol；Benzoesaeure-(7β-hydroxy-cholesten-(5)-yl-(3β)-ester)；3β-Benzoyloxy-cholesten-(5)-ol-(7β)；5-Cholestene-3beta,7beta-diol 3-benzoate；[(3S,7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] benzoate
• CAS: 17974-80-0
• 化学式: C₃₄H₅₀O₃
• 分子量: 506.769
• InChiKey: YAQOZGBTTMUPRW-FOYOODKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β,7β-cholest-5-ene-3,7-diol-3-benzoate 在 2,4,6-三甲基吡啶 、 三溴化磷 、 xylene 、 苯 作用下， 生成 7-脱氢苯甲酸胆固醇
  参考文献：
  名称：

  Evidence of toxic side effects of perfluorohexyloctane after vitreoretinal surgery as well as in previously established in vitro models with ocular cell types

  摘要：

  Background: Cases of ocular irritation have been observed after early clinical trials using perfluorohexyl octane (F6H8) as endotamponade. In our clinic two of three eyes developed severe inflammatory-like reactions after intermediate-term tamponade. These cases will be depicted, serving as background for the experimental study. To elucidate possible toxic effects of F6H8 on different ocular cell types and corneal tissue we applied our previously established in vitro models to investigate effects of F6H8 on cultured ocular cells in comparison with perfluorodecaline. Methods: Vitality and proliferation of cultured human corneal endothelial cells (HCEC) and human retinal pigment epithelial cells (RPE) were measured after incubation with F6H8 or perfluorodecaline for up to 5 days. Vitality was evaluated using the Live/Dead assay, and proliferation was determined according to BrdU incorporation. Additionally the endothelium of donor corneas was incubated with F6H8 for 5 days and endothelial cell morphology was documented. Results: After 5 days incubation with F6H8, cultures of RPE and HCEC showed significantly lower extinctions for vital cells as well as a non-significant decrease in proliferation compared with controls. Analysis by means of fluorescence microscopy after treatment with F6H8 or perfluorodecaline revealed decreased cell densities (F6H8 > perfluorodecaline) within contact areas. The endothelium of donor corneas incubated in presence of F6H8 developed circumscribed necrotic areas. Conclusions: Decreased amounts of vital cells cannot be explained solely by mechanical effects or nutritional deficit due to direct contact, since F6H8 has a lower specific weight than perfluorodecaline. The ability of the remaining cells to proliferate revealed that they were not irreversibly damaged. Due to the high lipophilicity of F6H8 interactions with cellular lipoprotein membranes as well as other toxic effects have to be considered and should further be investigated prior to clinical use.

  DOI：

  10.1007/s00417-002-0561-0
• 作为产物：
  描述：

  3β-benzoyloxy-cholest-5-en-7-one 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以65 %的产率得到3β,7β-cholest-5-ene-3,7-diol-3-benzoate
  参考文献：
  名称：

  含有类肉桂酸片段的新型胆固醇酯衍生物的半合成及杀虫活性。

  摘要：

  由于农用化学品的广泛使用导致了农药抗药性和生态环境问题的出现，因此迫切需要研究和开发用于作物保护的新替代品。为了发现基于天然产物的有效杀虫剂候选物，合成了一系列在 C-7 位含有肉桂酸样片段的新型胆固醇酯衍生物。一些衍生物表现出强大的杀虫活性。针对 Mythimna separata Walker，化合物 2a、Id、Ig 和 IIg 显示前体胆固醇的 2.1-2.4 倍生长抑制活性。针对林奈小菜蛾，化合物 Ig、IIf 和 IIi 的杀虫活性是胆固醇的 1.9-2.1 倍。这些结果将为未来合成基于胆固醇的衍生物作为农用化学品铺平道路。

  DOI：

  10.3390/molecules27238437

文献信息

• Ramachandran plot on the web
  作者：S.S. Sheik、P. Sundararajan、A.S.Z. Hussain、K. Sekar

  DOI：10.1093/bioinformatics/18.11.1548

  日期：2002.11.1

  Summary: A graphics package has been developed to display the main chain torsion angles phi, psi (φ, Ψ); (Ramachandran angles) in a protein of known structure. In addition, the package calculates the Ramachandran angles at the central residue in the stretch of three amino acids having specified the flanking residue types. The package displays the Ramachandran angles along with a detailed analysis output. This software is incorporated with all the protein structures available in the Protein Databank.

  Availability: This package is available over the world wide web at http://144.16.71.146/rp/ or http://dicsoft1.physics.iisc.ernet.in/rp.

  Contact: [e-mail]

  * To whom correspondence should be addressed.

  † This work is dedicated to Late Professor G. N. Ramachandran.

  摘要：已开发了一个图形软件包，用于显示已知结构蛋白质中的主链扭转角 phi, psi (φ, Ψ)（Ramachandran角度）。此外，该软件包计算了在具有指定侧链残基类型的三个氨基酸延伸中心残基处的Ramachandran角度。该软件包显示Ramachandran角度以及详细的分析输出。该软件已与蛋白质数据库中所有可用的蛋白质结构整合。 可用性：该软件包可通过全球网络访问，网址为 http://144.16.71.146/rp/ 或 http://dicsoft1.physics.iisc.ernet.in/rp。 联系方式：[e-mail] * 请将信函寄至。 † 本工作献给已故教授G. N. Ramachandran。
• [EN] STEROL DERIVATIVES AND USE THEREOF FOR TREATING DISEASES INVOLVING TRANSFORMED ASTROCYTE CELLS OR FOR TREATING MALIGNANT HAEMOPATHIES<br/>[FR] DÉRIVÉS DE STÉROL ET LEUR UTILISATION DANS LE TRAITEMENT DE MALADIES IMPLIQUANT DES CELLULES ASTROCYTES TRANSFORMÉES OU DANS LE TRAITEMENT D'HÉMOPATHIES MALIGNES
  申请人：BETA INNOV

  公开号：WO2013168096A1

  公开（公告）日：2013-11-14

  The invention relates to novel sterol derivatives, the preparation method thereof, pharmaceutical compositions containing them and use thereof for treating diseases involving transformed astrocyte cells or for treating malignant haemopathies. The invention in particular relates to the treatment of glioblastoma multiforme, as well as of other cancers, such as lymphomas, neuroblastomas and melanomas.

  本发明涉及新型甾醇衍生物、其制备方法、含有它们的药物组合物以及用于治疗涉及转化星形胶质细胞或治疗恶性血液病的用途。本发明特别涉及治疗多形性胶质母细胞瘤以及其他癌症，如淋巴瘤、神经母细胞瘤和黑色素瘤。
• Über die epimeren 7-Brom-cholesterylester und die Konfiguration der C-7-Substituenten in der Cholesterinreihe
  作者：H. Schaltegger、F. X. Müllner

  DOI：10.1002/hlca.19510340416

  日期：——

  vorliegen. Das 7α-Brom-cholesterylbenzoat ist das thermodynamisch labilere Epimere. Es wurden die Resultate mit analogen Fällen der Literatur verglichen. Aus der Übereinstimmung im chemischen und thermodynamischen Verhalten sowie der Übereinstimmung der molekularen Rotationsdifferenzen beim Vergleich mit anderen Steroiden mit Allylstruktur wurde mit Sicherheit geschlossen, dass in den positiv drehenden

  Es wurde gezeigt，Deurs bei der direkten Photobromierung von Cholesterinestern和bei der Bromierung mit Bromsuccinimid alsPrimärproduktenur7α-Brom-cholesterylesterentstehen，deren Struktur bewiesen wurde。在极化Lösungsmittelnzu einem Gleichgewicht中，死于beiden epimeren 7-溴-胆固醇胆固醇苯甲酸酯Epimerisieren，分别在70％7β-Brom-胆固醇胆固醇苯甲酸酯和30％7α-Brom-胆固醇胆固醇苯甲酸酯中。Das7α-溴-胆固醇基苯甲酸酯和热不稳定的Epimere。Es wurden die产生了Fällender Literatur
• Sterol derivatives and use thereof for treating diseases involving transformed astrocyte cells or for treating malignant haemopathies
  申请人：BETA INNOV

  公开号：US10800806B2

  公开（公告）日：2020-10-13

  Novel sterol derivatives, the preparation method thereof, pharmaceutical compositions containing them and use thereof for treating diseases involving transformed astrocyte cells or for treating malignant haemopathies. The treatment of glioblastoma multiforme, as well as of other cancers, such as lymphomas, neuroblastomas and melanomas is also described.

  新型甾醇衍生物、其制备方法、含有这些衍生物的药物组合物及其用于治疗涉及转化星形胶质细胞的疾病或治疗恶性血液病的用途。此外，还介绍了多形性胶质母细胞瘤以及其他癌症（如淋巴瘤、神经母细胞瘤和黑色素瘤）的治疗方法。
• Stereospecific Syntheses of the 7-Deuterio- and 7-Tritiocholesterols. The Mechanism of Enzyme-catalyzed Hydroxylation at a Saturated Carbon Atom
  作者：E. J. Corey、George A. Gregoriou

  DOI：10.1021/ja01521a053

  日期：1959.6

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