15α-Carboxymethyltestosterone | 65423-15-6

• 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
• 英文名称: 15α-Carboxymethyltestosterone
• 英文别名: 15-Carboxymethyltestosterone；2-[(8R,9S,10R,13S,14S,15R,17S)-17-hydroxy-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-15-yl]acetic acid
• CAS: 65423-15-6
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: JEFNUUSOAVNJKC-PVXGZESHSA-N

物化性质

• 沸点：
  541.7±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  <¹²⁵I>-Iodohistamine 、 15α-Carboxymethyltestosterone 在 sodium hydroxide 、 三正丁胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 15α-<2-(<¹²⁵I>Iodoimidazol-4'-yl)ethylcarbamoyl>methyltestosterone
  参考文献：
  名称：

  Characteristics of anti-testosterone antisera produced by bovine serum albumin conjugates of 15.ALPHA.- and 15.BETA.-carboxymethyltestosterone: Use of (125I)iodinated tracers.

  摘要：

  将[125I]碘代组胺与相应的15α-和15β-羧甲基睾酮（15α-和15β-CMT）、睾酮-3-（O-羧甲基）肟（T-3-CMO）和睾酮-17β-半琥珀酸盐（T-17-HS）结合，测试每种睾酮-[125I]碘代组胺衍生物作为睾酮免疫分析中放射性示踪剂的有效性。在用兔产生的抗15α-和15β-CMT抗血清与15α-和15β-CMT-牛血清白蛋白（BSA）结合物结合时，与含氚化睾酮（T-3H）的抗血清相比，含15α-和15β-CMT-[125I]碘代示踪剂的抗血清灵敏度较低，特异性也较低。另一方面，与T-3H相比，含T-3-CMO-[125I]碘代示踪剂的抗血清对5α-二氢睾酮（5α-DHT）的灵敏度高，但特异性低。T-17-HS-[125I]碘代示踪剂不与抗血清结合。在用兔产生的抗

  DOI：

  10.1248/cpb.38.951
• 作为产物：
  描述：

  15-bis(ethoxycarbonyl)methyl-3β-hydroxy-5-androsten-17-one 在 chromium(VI) oxide 、 sodium hydroxide 、 sodium tetrahydroborate 、 硫酸 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 0.17h， 生成 15α-Carboxymethyltestosterone
  参考文献：
  名称：

  Syntheses OF 15α- and 15β-carboxymethyltestosterone bovine serum albumin conjugates: Characteristics of the antisera to testosterone

  摘要：

  Syntheses of 15 alpha- and 15 beta-carboxymethyltestosterone (15 alpha- and 15 beta-CMT) were investigated in order to prepare testosterone-bovine serum albumin conjugates for radioimmunoassays of testosterone. A mixture of 15 alpha- and 15 beta-bis(ethoxycarbonyl)methyl-3 beta-hydroxy-5-androsten-17-one (IIa and IIb) obtained by a reaction of 3 beta-hydroxy-5,15-androstadien-17-one (I) and sodium diethyl malonate was oxidized to afford a mixture of 15 alpha- and 15 beta-bis(ethoxycarbonyl)methyl-4-androstene-3, 17-dione (Va and Vb). After the separation by silica gel chromatography, each epimer obtained was hydrolyzed by acid, followed by decarboxylation, and selective reduction of the 17-ketone to give 15 alpha- and 15 beta-CMT. The antisera, generated in rabbits by immunization with the bovine serum albumin (BSA) conjugates of 15 alpha- and 15 beta-CMT, respectively, exhibited high specificity for testosterone.

  DOI：

  10.1016/0039-128x(82)90037-x

文献信息

• 15Alpha-substituted estradiol carboxylic acid esters as locally active estrogens
  申请人：YALE UNIVERSITY

  公开号：US20040198711A1

  公开（公告）日：2004-10-07

  The present invention relates to analogs of estradiol, which, in their most preferred embodiment, act as locally active estrogens without significant systemic action. A series of 15&agr;-estradiol ester compounds is presented which exhibit excellent biological activity for use in pharmaceutical compositions for the treatment of symptomology associated with menopause. The present invention is therefore directed to compounds according to the structure: 1 where X is 2 R is H, a C 1 to C 5 alkyl group, optionally substituted with at least one halogen group, such as CH 2 CH 2 F, or other group (e.g., CH 2 CHF 2 , CH 2 CF 3 or CF 3 group); and m is from 0-5, preferably from 0-2.

  本发明涉及雌二醇的类似物，其在最理想的实施方式中作为局部活性雌激素而没有显著的全身作用。提出了一系列15α-雌二醇酯化合物，这些化合物表现出优异的生物活性，可用于治疗与更年期症状相关的药物组合物。因此，本发明涉及结构如下的化合物：其中X为R为H，C1至C5烷基，可选择地取代至少一个卤素基团，例如CH2CH2F，或其他基团（例如CH2CHF2，CH2 或CF3基团）；m为0-5，最好为0-2。
• US7015211B2
  申请人：——

  公开号：US7015211B2

  公开（公告）日：2006-03-21