(NZ)-N-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ylidene]hydroxylamine | 66514-00-9

• 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: (NZ)-N-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ylidene]hydroxylamine
• 英文别名: (3Z)-3-hydroxyimino-cholest-4-ene；(E)-cholest-4-en-3-one oxime；3-hydroximinocholest-4-ene；olesoxime；cholesten-(4)-one-(3)-seqcis-oxime；Cholesten-(4)-on-(3)-seqcis-oxim；Olesoxime, Z-
• CAS: 66514-00-9
• 化学式: C₂₇H₄₅NO
• 分子量: 399.66
• InChiKey: QNTASHOAVRSLMD-FCARAQADSA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  510.0±23.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (NZ)-N-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ylidene]hydroxylamine 在 乙醇 、 sodium 作用下， 生成 3β-Acetamidocholest-5-en
  参考文献：
  名称：

  Adverse reactions associated with echinacea: the Australian experience

  摘要：

  Background: Fifty percent of Australians use complementary and alternative medicines (other than vitamins) in any 12-month period, of which echinacea-containing products are increasingly popular. Recent reports have highlighted the risk of allergic reactions to complementary medicines in atopic patients.Objective: To determine the characteristics of adverse reactions linked to use of the popular herbal remedy echinacea.Methods: Five privately referred patients were evaluated by the authors in their office practice via skin prick testing (SPT) on the volar aspect of the forearm and radioallergosorbent test after adverse reactions to echinacea. As there was little published information on adverse reactions to echinacea, reports to the Australian Adverse Drug Reactions Advisory Committee were reviewed. Those suggestive of possible allergic reactions were evaluated in greater detail by anonymously surveying the healthcare professionals who had reported the cases and from one unreported case. Serum was collected for further analysis where possible.Results: Five cases of adverse reactions to echinacea were personally evaluated by the authors. Two patients suffered anaphylaxis and a third had an acute asthma attack 10 minutes after their first ever dose of echinacea. The fourth patient suffered recurrent episodes of mild asthma each time echinacea was ingested, and the fifth developed a maculopapular rash within 2 days of ingestion which recurred when rechallenged. Three of the patients had positive SPT results. Three reported repeated spontaneous "challenges" and symptoms after further ingestion of echinacea. Fifty-one Australian adverse drug reports implicating echinacea were also reviewed. There were 26 cases suggestive of possible immumoglobulin E-mediated hypersensitivity (4 anaphylaxis, 12 acute asthma, 10 urticaria/angioedema). Of these 26 patients, age ranged from 2 to 58 years, 78% were female and >50% were known to be atopic. Four were hospitalized, 4 reacted after their first known exposure, and I patient suffered multiple progressive systemic reactions. Twenty percent of 100 atopic subjects who had never taken echinacea also had positive SPT results to this substance when tested by one of the authors in his office practice.Conclusion: Some atopic subjects have positive SPT results to echinacea in the absence of known exposure. Atopic subjects are also overrepresented in those experiencing reactions to echinacea. The possibility that cross-reactivity between echinacea and other environmental allergens may trigger allergic reactions in "echinacea-naYve" subjects is supported by the Australian data. Given its widespread (and largely unsupervised) community use, even rare adverse events become inevitable. Atopic patients should be cautioned appropriately.

  DOI：

  10.1016/s1081-1206(10)63591-0
• 作为产物：
  描述：

  (Z)-cholest-4-en-3-one oxime 在 丁酸 作用下， 生成 (NZ)-N-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ylidene]hydroxylamine
  参考文献：
  名称：

  Stereoisomeric Oximes of Cholestenone

  摘要：

  DOI：

  10.1021/ja01866a055

文献信息

• Synthesis and evaluation of some steroidal oximes as cytotoxic agents: Structure/activity studies (I)
  作者：Jian-Guo Cui、Lei Fan、Li-Liang Huang、Hong-Li Liu、Ai-Min Zhou

  DOI：10.1016/j.steroids.2008.09.003

  日期：2009.1

  hydroximino on ring A and B displayed remarkable distinct cytotoxicities against a diversity of cancer cell types. Presence of an oxime group on ring B and a hydroxy on ring A or B resulted in a higher cytotoxicity than other structural motifs. In addition, a cholesterol-type side chain at position 17 was required for the biological activity. Our findings provide new evidence showing the relationship

  化合物的侧链在其生物学功能中起着重要作用。在我们的研究中，我们发现具有不同侧链和羟基氨基在环 A 和 B 上位置的羟基亚氨基类固醇衍生物对多种癌细胞类型显示出显着不同的细胞毒性。环 B 上的肟基团和环 A 或 B 上的羟基导致比其他结构基序更高的细胞毒性。此外，生物活性需要第 17 位的胆固醇型侧链。我们的研究结果提供了新的证据，表明化学结构与生物功能之间的关系。从研究中获得的信息可能有助于设计新型化疗药物。
• Synthesis and In Vitro Studies of O-Alkylaminoethylated Derivatives of 3E-Hydroximinocholestene as Potent and Selective Antileukemic Agents
  作者：Amruta Suryan、Ranju Bansal

  DOI：10.1007/s11094-020-02297-6

  日期：2020.12

  New O-alkylaminoethylated derivatives of 3-hydroximinocholestene were synthesised and studied for in vitro cytotoxic effects. The obtained oily oxime ethers were solidified by preparing their oxalate salts. The steroidal compounds were screened against 60 human cancer cell lines at 10 μM. The study indicated that the compounds display selective cytotoxicity against leukemia cell lines. Dimethylamine

  合成了 3-羟基氨基胆甾醇的新 O-烷基氨基乙基化衍生物，并研究了其体外细胞毒性作用。所得油状肟醚通过制备草酸盐固化。在 10 μM 下针对 60 种人类癌细胞系筛选了甾体化合物。研究表明，这些化合物对白血病细胞系具有选择性的细胞毒性。二甲胺 (7a) 和吡咯烷 (7d) 衍生的 O-烷基化甾体草酸盐对 CCRF-CEM 白血病癌细胞系的生长抑制百分比分别为 73.36% 和 69.97%。还估计了新类固醇的分配系数值以研究亲脂性与生物活性的相关性。当用化合物 7a 和 7d 处理时，白血病细胞系的总体生长抑制百分比分别为 42% 和 41%。
• [EN] COMPOSITIONS FOR TREATING SPINAL MUSCULAR ATROPHY<br/>[FR] COMPOSITIONS POUR LE TRAITEMENT D'UNE AMYOTROPHIE SPINALE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2017080967A1

  公开（公告）日：2017-05-18

  The present invention provides pharmaceutical compositions comprising a compound of formula (I) wherein A, R1, R2 and R3 are as described herein, as well as pharmaceutically acceptable salts thereof. Further the present invention is concerned with the manufacture of the pharmaceutical compositions comprising a compound of formula (I) and their use as medicaments.

  本发明提供了包含式(I)化合物的药物组合物，其中A、R1、R2和R3如本文所述，并且其药学上可接受的盐。此外，本发明涉及制备包含式(I)化合物的药物组合物以及它们作为药物的用途。
• NOVEL CHOLEST-4-EN-3-ONE OXIME DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME, AND PREPARATION METHOD
  申请人：Pruss Rebecca

  公开号：US20110224180A1

  公开（公告）日：2011-09-15

  The present invention relates to novel chemical compounds, in particular cholest-4-en-3-one oxime derivatives and to the use thereof as medicaments, especially as cytoprotective medicaments, in particular neuroprotective, cardioprotective and/or hepatoprotective medicaments.

  本发明涉及新型化合物，特别是胆甾-4-烯-3-酮肟衍生物，并将其用作药物，尤其是细胞保护药物，特别是神经保护、心脏保护和/或肝脏保护药物。
• Use of derivatives of cholest-4-en-3-one as medicaments, pharmaceutical compositions containing same, novel derivatives and preparation method thereof
  申请人：Bordet Thierry

  公开号：US20060217358A1

  公开（公告）日：2006-09-28

  Compound of formula I where X=O or ═N—OH group, R represents a group chosen from A=hydrogen or together with B a carbon-carbon bond, B=hydrogen, hydroxy or together with A a carbon-carbon bond, C, D, E, F=hydrogen or together with D a carbon-carbon bond, or the one of its addition salts with pharmaceutically acceptable acids, with the exception of a few compounds, as a medicament, use in particular as neuroprotectors, novel compounds of formula I and pharmaceutical compositions.

  化合物I的化学式如下，其中X可以是O或═N—OH基团，R代表从以下组中选择的一种：A=氢或与B一起形成碳-碳键，B=氢、羟基或与A一起形成碳-碳键，C、D、E、F=氢或与D一起形成碳-碳键，或其与药学上可接受的酸的一种或多种加成盐，除了少数化合物外，作为药物，特别是作为神经保护剂，化合物I的新型化合物和制药组合物。