N-cholest-4-en-3α-yl-acetamide | 66500-90-1

• 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: N-cholest-4-en-3α-yl-acetamide
• 英文别名: N-Cholest-4-en-3α-yl-acetamid；3α-Acetamino-cholesten-(4)；3α-Acetamino-cholest-4-en
• CAS: 66500-90-1
• 化学式: C₂₉H₄₉NO
• 分子量: 427.714
• InChiKey: XGOWVOGITDLHGV-GPJXBBLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.53
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-cholest-4-en-3α-yl-acetamide 在 溶剂黄146 、 铂 作用下， 生成 N-(5β-cholestan-3α-yl)-acetamide
  参考文献：
  名称：

  Shoppee et al., Journal of the Chemical Society, 1956, p. 1649,1653

  摘要：

  DOI：
• 作为产物：
  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 N-cholest-4-en-3α-yl-acetamide 、 3β-Acetamino-cholest-4-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

文献信息

• STEROIDS: III. THE EPIMERIC N-ACETYL-3-AMINOCHOLEST-4- AND -5-ENES
  作者：R. A. B. Bannard、A. F. McKay

  DOI：10.1139/v55-137

  日期：1955.6.1

  Lithium aluminum hydride reduction of the oximes of 3-ketocholest-4- and -5-enes gave mixtures of amines. These amines on acetylation and separation gave respectively N-acetyI-3(α)-aminocholest-5-ene, N-acetyl-3(β) aminocholest-5-ene, N-acetyl-3(α)-aminocholest-4-ene, and N-acetyl-3(β)-aminocholest-4-ene. The N-acetyl-3(α)-aminocholest-5-ene (m.p. 184.5 °C.) was shown to be identical with the cholesterylacetamide obtained by the acetylation of the degradation product from N-benzyl-3(α)-aminocholest-5-ene (m.p. 90-91 °C).

  3-酮胆甾-4-烯和-5-烯的肟经过氢化铝锂还原后，产生了混合胺。这些胺在乙酰化和分离后分别得到N-乙酰基-3（α）-氨基胆甾-5-烯，N-乙酰基-3（β）氨基胆甾-5-烯，N-乙酰基-3（α）-氨基胆甾-4-烯和N-乙酰基-3（β）-氨基胆甾-4-烯。N-乙酰基-3（α）-氨基胆甾-5-烯（熔点184.5℃）被证明与从N-苯甲基-3（α）-氨基胆甾-5-烯（熔点90-91℃）的降解产物乙酰化得到的胆固醇乙酰胺相同。