cholestanyl 2-chloroacetate | 108694-75-3

• 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: cholestanyl 2-chloroacetate
• 英文别名: dihydrocholesteryl chloroacetate；5α-cholestan-3β-yl chloroethanoate；chloroacetic acid-(5α-cholestanyl-(3β)-ester)；3β-Chloracetoxy-5α-cholestan；(10S)-3c-Chloracetoxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(5tH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；Chloressigsaeure-(5α-cholestanyl-(3β)-ester)；cholestanyl monochloroacetate；[(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] 2-chloroacetate
• CAS: 108694-75-3
• 化学式: C₂₉H₄₉ClO₂
• 分子量: 465.16
• InChiKey: WUBOZGDSEKAKCR-DVNBGNEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.26
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  cholestanyl 2-chloroacetate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 5α-cholestan-3β-yl aminoethanoate
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of water-soluble, dendritic derivatives of epimeric 5α-cholestan-3-amines and 5α-cholestan-3-yl aminoethanoates

  摘要：

  To examine the effect of negatively charged steroidal amphiphiles on antimicrobial activity, two pairs of epimeric, dendritic tricarboxylato amphiphiles -4-(2-carboxyethyl)-4-[3-(5 alpha-cholestan-3-yl)ureido]heptanedioic acid (1) and 4-(2-carboxyethyl)-4-[3-(5 alpha-cholestan-3-yloxycarbonylmethyl)ureido]heptanedioic acid (2) - were synthesized. Abroad antimicrobial screen of 11 microbes revealed that these amphiphiles only showed good activity against a methicillin -resistant isolate of Staphylococcus aureus (MRSA) and modest activity against an unrelated strain of S aureus The best activity a minimal inhibitory concentration (MIC) of 27 mu M, was found for the 3 beta epimer of 1 against MRSA. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.04.001
• 作为产物：
  描述：

  3β-胆甾烷醇 、 氯乙酸 反应 3.0h， 以96%的产率得到cholestanyl 2-chloroacetate
  参考文献：
  名称：

  [EN] DERIVATIVES COMPRISING STEROLS AND/OR STANOLS AND SPECIFIC CLASSES OF ANTI-INFLAMMATORY AGENTS AND USE THEREOF IN TREATING OR PREVENTING CARDIOVASCULAR DISEASE
  [FR] DERIVES COMPRENANT DES STEROLS ET/OU DES STANOLS ET DES CLASSES SPECIFIQUES D'AGENTS ANTI-INFLAMMATOIRES, ET UTILISATION DESDITS DERIVES POUR LE TRAITEMENT OU LA PREVENTION DE MALADIES CARDIOVASCULAIRES

  摘要：

  本发明一方面提供了新颖的衍生物，包括甾醇和/或甾烷醇以及从水杨酸和芳烷酸中选择的非甾体抗炎药（NSAID），包括这些衍生物的盐，并具有以下一种或多种公式：a) R2-(CH2)n-CO-OR b) R2-R c) R2-CO-CO-OR d) 公式 (I)，其中R是甾醇或甾烷醇部分，R2来自水杨酸或芳烷酸，n=1-5。还提供了包含一种或多种这些新颖衍生物的药物组合物，以及治疗或预防心血管疾病及其基础条件的方法，包括但不限于动脉粥样硬化、高胆固醇血症、高脂血症、高血压、血栓形成、冠心病，以及治疗和减少炎症的方法，包括冠状动脉斑块炎症、细菌诱导的炎症、病毒诱导的炎症以及与急性疼痛和手术程序相关的炎症，该方法包括向动物，尤其是人类，投予一种或多种这些化合物或其生物学可接受的盐的非毒性和治疗有效量。

  公开号：

  WO2004029068A1

文献信息

• Synthetic Models for Transmembrane Channels: Structural Variations That Alter Cation Flux
  作者：Oscar Murillo、Shigeru Watanabe、Akio Nakano、George W. Gokel

  DOI：10.1021/ja00134a011

  日期：1995.7

  Twelve novel bis- or tris(macrocyclic) compounds have been designed as models for cation-conducting channels that function in phospholipid bilayer vesicle membranes. In general, the channel model systems have the structure ''sidearm-crown-spacer-crown-spacer-crown-sidearm'', although certain features have been altered from compound to compound to assess the structure-activity relationship. Two additional compounds have been prepared exclusively as controls. The ionophores have been incorporated into the membranes either by warming the compound with the preformed vesicle or by incorporation during vesicle formation. The two methods gave identical results within experimental error. Cation flux was assessed by two different analytical methods. In one case, the fluorescent dye pyranine was encapsulated within vesicles containing ionophore. Proton transport was then monitored by changes in dye fluorescence with time following an acid pulse. Ionophoretic activity far most of the compounds was studied using a dynamic NMR method in which the flux rate of Na-23(+) through the bilayer was monitored. All NMR studies were done in conjunction with gramicidin as a control to minimize experimental variations from run to run. Several of the synthetic ionophores showed cation conduction of as much as 40% of the activity of gramicidin. Apparently, small structural changes significantly altered flux rates and two known carriers closely related to the channel formers failed to exhibit measurable transport under comparable conditions.
• Topalǎ, Carmen; Meltzer, Viorica; Pincu, Elena, Revue Roumaine de Chimie, 2002, vol. 47, # 6, p. 539 - 542
  作者：Topalǎ, Carmen、Meltzer, Viorica、Pincu, Elena、Drǎghici, Constantin

  DOI：——

  日期：——
• Abel, Ernesto; Fedders, Megan F.; Gokel, George W., Journal of the American Chemical Society, 1995, vol. 117, # 4, p. 1265 - 1270
  作者：Abel, Ernesto、Fedders, Megan F.、Gokel, George W.

  DOI：——

  日期：——
• [EN] DERIVATIVES COMPRISING STEROLS AND/OR STANOLS AND SPECIFIC CLASSES OF ANTI-INFLAMMATORY AGENTS AND USE THEREOF IN TREATING OR PREVENTING CARDIOVASCULAR DISEASE<br/>[FR] DERIVES COMPRENANT DES STEROLS ET/OU DES STANOLS ET DES CLASSES SPECIFIQUES D'AGENTS ANTI-INFLAMMATOIRES, ET UTILISATION DESDITS DERIVES POUR LE TRAITEMENT OU LA PREVENTION DE MALADIES CARDIOVASCULAIRES
  申请人：FORBES MEDI TECH INC

  公开号：WO2004029068A1

  公开（公告）日：2004-04-08

  The present invention provides, in one aspect, novel derivatives comprising sterols and/or stanols and an NSAID selected from salicylic acids and arylalkanoic acids, including salts of these derivatives, and having one or more of the following formulae: a) R2-(CH2)n-CO-OR b) R2-R c) R2-CO-CO-OR d) formula (I), wherein R is a sterol or stanol moiety, R2 is derived from a salicylic acid or an arylalkanoic acid and n=1-5. Also provided are pharmaceutical compositions comprising one or more of these novel derivatives and methods of treating or preventing cardiovascular disease and its underlying conditions including, without limitation, atherosclerosis, hypercholesterolemia, hyperlipidemia, hypertension, thrombosis, coronary artery disease, and for treating and reducing inflammation including coronary plaque inflammation, bacterial-induced inflammation, viral induced inflammation and inflammation associated with acute pain and surgical procedures which comprises administering to an animal, particularly a human, a non-toxic and therapeutically effective amount of one or more of these compounds or a biologically acceptable salt thereof.

  本发明一方面提供了新颖的衍生物，包括甾醇和/或甾烷醇以及从水杨酸和芳烷酸中选择的非甾体抗炎药（NSAID），包括这些衍生物的盐，并具有以下一种或多种公式：a) R2-(CH2)n-CO-OR b) R2-R c) R2-CO-CO-OR d) 公式 (I)，其中R是甾醇或甾烷醇部分，R2来自水杨酸或芳烷酸，n=1-5。还提供了包含一种或多种这些新颖衍生物的药物组合物，以及治疗或预防心血管疾病及其基础条件的方法，包括但不限于动脉粥样硬化、高胆固醇血症、高脂血症、高血压、血栓形成、冠心病，以及治疗和减少炎症的方法，包括冠状动脉斑块炎症、细菌诱导的炎症、病毒诱导的炎症以及与急性疼痛和手术程序相关的炎症，该方法包括向动物，尤其是人类，投予一种或多种这些化合物或其生物学可接受的盐的非毒性和治疗有效量。
• Synthesis and antimicrobial evaluation of water-soluble, dendritic derivatives of epimeric 5α-cholestan-3-amines and 5α-cholestan-3-yl aminoethanoates
  作者：Eko W. Sugandhi、Carla Slebodnick、Joseph O. Falkinham、Richard D. Gandour

  DOI：10.1016/j.steroids.2007.04.001

  日期：2007.7

  To examine the effect of negatively charged steroidal amphiphiles on antimicrobial activity, two pairs of epimeric, dendritic tricarboxylato amphiphiles -4-(2-carboxyethyl)-4-[3-(5 alpha-cholestan-3-yl)ureido]heptanedioic acid (1) and 4-(2-carboxyethyl)-4-[3-(5 alpha-cholestan-3-yloxycarbonylmethyl)ureido]heptanedioic acid (2) - were synthesized. Abroad antimicrobial screen of 11 microbes revealed that these amphiphiles only showed good activity against a methicillin -resistant isolate of Staphylococcus aureus (MRSA) and modest activity against an unrelated strain of S aureus The best activity a minimal inhibitory concentration (MIC) of 27 mu M, was found for the 3 beta epimer of 1 against MRSA. (c) 2007 Elsevier Inc. All rights reserved.