穿贝海绵甾醇22,23-二氢多孔甾醇24-γ-乙基胆固醇 | 83-47-6

• 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
• 中文名称: 穿贝海绵甾醇22,23-二氢多孔甾醇24-γ-乙基胆固醇
• 中文别名: γ-谷甾醇
• 英文名称: clionasterol
• 英文别名: γ-sitosterol；β-sitosterol；sitosterol；gamma-sitosterol；(3β,24S)-stigmast-5-en-3-ol；γ‐sitosterol；stigmast-5-en-3-ol；beta-sitosterol；(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 83-47-6
• 化学式: C₂₉H₅₀O
• 分子量: 414.715
• InChiKey: KZJWDPNRJALLNS-FBZNIEFRSA-N

物化性质

• 沸点：
  473.52°C (rough estimate)
• 密度：
  0.9540 (rough estimate)
• 熔点：
  147 °C
• 物理描述：
  Solid
• 保留指数：
  3351.3;3290
• 稳定性/保质期：
  存在于烤烟烟叶、白肋烟烟叶、香料烟烟叶、烟气中。单水合物。

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

制备方法与用途

合成制备方法

1. 烟草中的FC、8、32和41以及BU（1）；大豆油的主要甾醇是从玉米油中分离获得的，也可以从中国蟾蜍的毒液中提取。

2. 该化合物可以从乙醇中结晶得到片晶。

反应信息

• 作为反应物：
  描述：

  穿贝海绵甾醇22,23-二氢多孔甾醇24-γ-乙基胆固醇 在 臭氧 、 二甲基硫 、 lithium hydroxide 作用下， 以 乙醚 、 甲醇 为溶剂， 反应 24.08h， 生成 (3R,3aR,5aS,5bR,8S,10aS,10bS)-3-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-8-hydroxy-3a,5b-dimethyl-1,2,3,4,5,5a,6,7,8,9,10a,10b-dodecahydrocyclopenta[a]fluorene-10-carbaldehyde
  参考文献：
  名称：

  Synthesis and in vitro biological evaluation of ring B abeo-sterols as novel inhibitors of Mycobacterium tuberculosis

  摘要：

  A series of 3b-hydroxy steroid analogues possessing a contracted cyclopentane B-ring were prepared based on the initial activity screening of a recently reported naturally occurring marine 5(6-->7) abeo-sterol against Mycobacterium tuberculosis. All of the novel ring B abeo-sterols synthesized showed good inhibitory activity, whereas none of the starting steroids based on the common 3 beta-hydroxy-Delta(5)-cholestane nucleus, proved to be active. Therefore, the 5(6-->7) abeo-sterol nucleus present in compounds 3, 5, 7, 9, and 11 represents a novel scaffold for the development of new antitubercular agents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.029
• 作为产物：
  描述：

  (22R)-6β-methoxy-3α,5-cyclo-27-nor-5α-cholest-23-yn-22-ol 在 palladium on activated charcoal 、 Lindlar's catalyst 喹啉 、 lithium aluminium tetrahydride 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 水 、 乙酸乙酯 、 xylene 为溶剂， 反应 8.0h， 生成 穿贝海绵甾醇22,23-二氢多孔甾醇24-γ-乙基胆固醇
  参考文献：
  名称：

  Fujimoto, Yoshinori; Kimura, Miki; Khalifa, Fathy A. M., Chemical and pharmaceutical bulletin, 1984, vol. 32, # 11, p. 4372 - 4381

  摘要：

  DOI：

文献信息

• Novel sterol/stanol phosphorylnitroderivatives and use thereof in treating or preventing cardiovascular disease, its underlying conditions and other disorders
  申请人：Orchansky Liliana Patricia

  公开号：US20070232688A1

  公开（公告）日：2007-10-04

  Sterol and stanol phosphorylnitro derivatives and their use in treating or preventing cardiovascular disease, its underlying conditions and other disorders are disclosed. The disclosed compounds include a phosphate linker, at least one moiety that releases nitric oxide (NO), and a sterol or stanol moiety. Some compounds additionally include an ascorbyl moiety to make the compound more readily soluble in aqueous and non-aqueous media.

  甾醇和甾酚磷酸硝基衍生物及其在治疗或预防心血管疾病、其潜在病症和其他疾病中的用途被披露。所披露的化合物包括一个磷酸酯连接物、至少一个释放一氧化氮（NO）的基团，以及一个甾醇或甾酚基团。一些化合物还包括抗坏血酸基团，以使化合物在水性和非水性介质中更容易溶解。
• Composition Containing Novel Glutamic Acid Derivative And Block Copolymer, And Use Thereof
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：US20200190101A1

  公开（公告）日：2020-06-18

  Provided is a pharmaceutical preparation that is suitable for more effectively exhibiting the efficacy of a glutamic acid derivative, which is a GGT-recognizable prodrug, by producing a composition including a glutamic acid derivative capable of rapidly releasing a physiologically active substance by being recognized by GGT, or a pharmacologically acceptable salt thereof; and a block copolymer in which a polyethylene glycol segment is linked to a polyamino acid segment with a hydrophobic group. Particularly, the composition based on a glutamic acid derivative that uses an antitumor compound as a physiologically active substance is capable of effectively accumulating the glutamic acid derivative at a tumor affected area, exhibits a superior effect against tumors, and is capable of suppressing the release of a physiologically active substance in bone marrow tissue where the expression ratio of GGT is low. Therefore, side effects such as myelosuppression, which pose a problem in the use of antitumor drugs, may be avoided.

  提供的是一种药物制剂，适用于更有效地展现谷氨酸衍生物的功效，该衍生物是一种GGT可识别的前药，通过制备包括一种能够被GGT识别从而快速释放生理活性物质的谷氨酸衍生物或其药理学可接受的盐的组合物；以及一种嵌段共聚物，其中聚乙二醇段与一个疏水基团连接到一个聚氨基酸段。特别是，基于谷氨酸衍生物的组合物使用抗肿瘤化合物作为生理活性物质，能够有效地在受肿瘤影响的区域积累谷氨酸衍生物，对肿瘤具有优越效果，并能够抑制在GGT表达比例较低的骨髓组织中释放生理活性物质。因此，可以避免使用抗肿瘤药物时可能出现的骨髓抑制等副作用。
• 방사선 치료 증폭을 위한 사이토스테롤-독소루비신 유도체 및 이를 유효성분으로 포함하는 암 질환 예방 또는 치료용 조성물
  申请人：Kyungpook National University Industry-Academic Cooperation Foundation 경북대학교 산학협력단(220040016844) BRN ▼504-82-09678

  公开号：KR20200086541A

  公开（公告）日：2020-07-17

  본 발명은 방사선 치료 증폭을 위한 사이토스테롤-독소루비신 유도체 및 이를 유효성분으로 포함하는 암 질환 예방 또는 치료용 조성물에 관한 것으로, 본 발명에서는 β-사이토스테롤을 이용하여 독소루비신 유도체로서 Sito-dox A 및 Sito-dox B를 합성하였으며, 상기 Sito-dox A는 독소루비신 보다 우수한 항암 효과, 및 방사선 요법과의 병용 치료에서 시너지 효과를 나타내고, Sito-dox B는 세포 독성을 나타내지 않았으나, 방사선 요법과의 병용 치료에서 종양 붕괴 현상을 나타내는 것을 확인하였다. 즉, 본 발명의 β-사이토스테롤을 이용하여 합성된 독소루비신 유도체는 방사선 요법과 병용 치료 시, 항암 치료 효과를 증폭시킬 수 있고, 독소루비신의 체내 짧은 체류 시간과 빠른 용출의 단점을 극복할 수 있는 바, 보다 효과적인 암 질환 예방 또는 치료용 약학 조성물, 방사선 치료 민감제용 약학 조성물 등으로 유용하게 활용될 수 있다. 더불어, 사이토스테롤과 구조 및 물성이 유사한 콜릭산, 글리코콜릭산, 타우로콜릭산, 디옥시콜릭산, 케노데옥시콜릭산, 글리코케노디옥시콜릭산, 타우로케노데옥시콜릭산, 콜레스테롤 및 리토콜릭산 등의 지질로 치환된 독소루비신 유도체에서도 사이토스테롤로 치환된 독소루비신 유도체와 유사한 암 치료 효과를 보일 것으로 기대된다.

  This is the Chinese translation of the text you provided: 该发明涉及一种用于放射线治疗增强的鞘固醇-毒素鲁比汀衍生物及其作为有效成分包含在癌症预防或治疗组合物中，该发明利用β-鞘固醇合成了毒素鲁比汀衍生物Sito-dox A和Sito-dox B，其中Sito-dox A表现出比毒素鲁比汀更优越的抗癌效果，并在与放射线疗法联合治疗中显示出协同效应，Sito-dox B虽未表现出细胞毒性，但在与放射线疗法联合治疗中显示出肿瘤崩解现象。换言之，利用本发明的β-鞘固醇合成的毒素鲁比汀衍生物在放射线疗法与联合治疗时，可以增强抗癌治疗效果，并克服毒素鲁比汀在体内短暂停留时间和快速排出的缺点，因此可以更有效地用于癌症预防或治疗的药物组合物，放射线治疗敏感剂用药物组合物等。此外，预计在鞘固醇替代毒素鲁比汀衍生物中，如胆酸、甘露醇胆酸、牛磺酸胆酸、脱氧胆酸、肝胆酸、甘露糖肝胆酸、牛磺酸肝胆酸、胆固醇和脂肪酸等脂质中也替换为鞘固醇的毒素鲁比汀衍生物将表现出类似于鞘固醇替代毒素鲁比汀衍生物的抗癌治疗效果。
• Direct Synthesis of α-Amino Nitriles from Sulfonamides via Base-Mediated C–H Cyanation
  作者：Shasha Shi、Xianyu Yang、Man Tang、Jiefeng Hu、Teck-Peng Loh

  DOI：10.1021/acs.orglett.1c01232

  日期：2021.5.21

  Herein, we disclose a transition-metal-free reaction system that enables α-cyanation of sulfonamides through C–H bond cleavage for the preparation of α-amino nitriles, including difficult-to-access all-alkyl α-tertiary scaffolds. More than 50 substrate examples prove a wide functional group tolerance. Additionally, its synthetic practicality is highlighted by gram-scalability and the late-stage modification

  在这里，我们公开了一种无过渡金属的反应体系，该体系可使磺酰胺通过C–H键断裂进行α-氰化，以制备α-氨基腈，包括难以接近的全烷基α-叔骨架。超过50个底物实例证明了广泛的官能团耐受性。另外，其合成实用性通过克可缩放性和天然化合物的后期修饰得到突出。机理实验表明，该过程涉及通过碱促进的HF的消除而原位形成亚胺中间体。
• Visible-Light-Induced Oxazoline Formations from <i>N</i>-Vinyl Amides Catalyzed by an Ion-Pair Charge-Transfer Complex
  作者：Rui Sun、Xiao Yang、Yicen Ge、Jintong Song、Xueli Zheng、Maolin Yuan、Ruixiang Li、Hua Chen、Haiyan Fu

  DOI：10.1021/acscatal.1c01755

  日期：2021.9.17

  catalysis which often involves transition-metal complexes, conjugated organic dyes, or electron donor–acceptor complexes, herein, the use of ion-pair charge-transfer (IPCT) complex-induced visible-light photoredox catalytic reactions are described, wherein the cyclization–methoxylation of N-vinyl amides in methanol was achieved under irradiation with blue LEDs. The reaction employs a heteroarenium iodide

  可见光光氧化还原催化在典型热条件下无法进行的各种反应中起着重要作用。与通常涉及过渡金属配合物、共轭有机染料或电子供体 - 受体配合物的常见可见光光氧化还原催化明显不同，此处使用离子对电荷转移 (IPCT) 配合物诱导可见光光氧化还原催化描述了反应，其中N的环化 - 甲氧基化- 乙烯酰胺甲醇溶液是在蓝光 LED 照射下获得的。该反应使用碘化杂芳烃作为光催化剂，并且可以扩展到环化-烷氧基化、-酰氧基化和-羟基化。该协议为各种恶唑啉衍生物提供了一种环保的合成路线。紫外-可见光谱和对照实验的机理研究证实了碘化杂芳烃在可见光区存在 IPCT 吸收带，这是观察到的反应性的原因。