雄甾-3-酮-4-烯-17bata-羧酸甲酯 | 2681-55-2

• 物质功能分类: 天然产物 - 甾体化合物
• 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: 雄甾-3-酮-4-烯-17bata-羧酸甲酯
• 中文别名: 雄甾-3-酮-4-烯-17β-羧酸甲酯；F4(3-酮-4-雄烯-17Β-羧酸甲酯)(136,000)；3-酮-4-雄烯-17beta-羧酸甲酯；甲基-3-氧代-4-雄烯-17-羧酸；雄甾-3-酮-4-烯-17Beta-羧酸甲酯
• 英文名称: 3-oxo-androst-4-ene-17β-carboxylic acid methyl ester
• 英文别名: methyl 3-oxo-androst-4-ene-17β-carboxylate；Methyl 3-oxo-4-androstene-17beta-carboxylate；methyl (8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-17-carboxylate
• CAS: 2681-55-2
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: XWFWMYFLNHTEBF-YFWFAHHUSA-N

物化性质

• 熔点：
  130-131 °C
• 沸点：
  441.8±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2937290090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  雄甾-3-酮-4-烯-17bata-羧酸甲酯 在 吡啶 、 氢氧化钾 、 氯化亚砜 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 8.0h， 生成 3-oxoandrost-4-ene-17β-carboxylic acid chloride
  参考文献：
  名称：

  Anti-AIDS agents. Part 36: 1 17-carboxylated steroids as potential anti-HIV agents

  摘要：

  In our search for novel anti-HIV agents, seven 17-carboxylated steroid derivatives were synthesized and evaluated as potential anti-HIV agents. Compound 13 exhibited potent anti-HIV activity in acutely infected H9 lymphocytes with EC50 and therapeutic index values of 0.8 microM and 300, respectively.

  DOI：

  10.1016/s0968-0896(99)00169-8
• 作为产物：
  描述：

  孕烯醇酮醋酸酯 在 盐酸 、 sodium hypobromide 、 环己酮 、 aluminum isopropoxide 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 雄甾-3-酮-4-烯-17bata-羧酸甲酯
  参考文献：
  名称：

  Synthesis of 4-trifluoromethylsteroids: A novel class of steroid 5α-reductase inhibitors

  摘要：

  DOI：

  10.1016/s0960-894x(97)10156-1

文献信息

• Preparation of 4-aza-17-substituted-5.alpha.-androstan-3-ones useful as
  申请人：Merck & Co., Inc.

  公开号：US04220775A1

  公开（公告）日：1980-09-02

  A method of preparing a compound of the formula: ##STR1## where Formula (I) may also have the structure of partial Formula (III); wherein, ##STR2## R' is hydrogen or methyl; R" is hydrogen or .beta.-methyl; R'" is .beta.-methyl or hydroxy; Z is (1) oxo; (2) .beta.-hydrogen and .alpha.-hydroxy; or .alpha.-hydrogen or .alpha.-hydroxyl and (3) (Y).sub.n Q where n=0 or 1, Y is a straight or branched hydrocarbon chain of 1 to 12 carbon atoms and Q is ##STR3## where R.sup.8 is, ##STR4## where the dashed bond replaces the 17.alpha. hydrogen; (6) cyano; or (7) tetrazolyl; and pharmaceutically acceptable salts of the above compounds; CHARACTERIZED IN THAT (I.) a compound of the formula: ##STR5## , where A has the meanings above except --CH.dbd.CH--, is (1) treated with an oxidizing agent at reduced temperatures to form the corresponding 5-oxo-3,5-seco-androstan-3-oic acid compound; (2) treating the product of step (1) with an amine of formula: R.sup.1 NH.sub.2 to form the corresponding 4-aza-5-androsten-3-one compound substituted in the 4-position with R.sup.1 ; and (3) treating the product of step (2) with hydrogen under catalytic conditions to form the compound of Formula I and I & II wherein B is ##STR6## (II.) and where it is desired to prepare compounds of Formula I wherein B is ##STR7## additionally carrying out the following steps on the products prepared by the procedures in (I.) above: (1) alkylating the lactim carbonyl by treating it with trialkyloxonium tetrafluoroborate to form the corresponding alkyl iminium ether, i.e., the compound of Formula I where B is as above and R.sup.4 =OR.sup.5 ; (2) treating the product of step (1) with an amine of formula HNR.sup.6 R.sup.7 followed by treatment with a mineral acid to form the compound of Formula I where B is as above and R.sup.4 =NR.sup.6 R.sup.7 ; (III.) and where it is desired to prepare compounds of Formula I wherein A is --CH.dbd.CH--, additionally carrying out the following steps on the products prepared by the procedures in (I.) above: (1) treating the 1,2 saturated compound with lithium diisopropyl amide to form the corresponding enolate; (2) treating the enolate of step (1) in situ with diphenyldisulfide to form the corresponding .alpha.-phenylthio compound; (3) oxidizing the product of step (2) to form the corresponding sulfoxide compound; and (4) heating the product of step (3) to form the compound of Formula I wherein A is --CH.dbd.CH--.

  将公式为：##STR1##的化合物制备方法翻译成中文：其中，公式（I）也可能具有部分公式（III）的结构；其中，##STR2## R'为氢或甲基；R"为氢或β-甲基；R'"为β-甲基或羟基；Z为（1）氧代；（2）β-氢和α-羟基；或α-氢或α-羟基和（3）（Y）.sub.n Q，其中n=0或1，Y为1至12个碳原子的直链或支链烃链，Q为##STR3##，其中R.sup.8为，##STR4##，其中虚线键替代17α氢；（6）氰基；或（7）四唑基；以及上述化合物的药用盐；其特征在于（I.）公式为：##STR5##的化合物，其中A具有上述含义，除了--CH.dbd.CH--，经过以下步骤：（1）在较低温度下用氧化剂处理，形成相应的5-氧代-3,5-戊二烯基雄烷-3-酸化合物；（2）用式为R.sup.1 NH.sub.2的胺处理步骤（1）的产物，形成在4位用R.sup.1取代的相应的4-氮杂-5-雄烷-3-酮化合物；（3）用催化条件下的氢处理步骤（2）的产物，形成公式I和I & II的化合物，其中B为##STR6##（II.）并且如果希望制备B为##STR7##的公式I的化合物，另外对（I.）中的程序制备的产物进行以下步骤：（1）通过用三烷氧氟硼酸盐处理酮内酰基，烷基化，形成相应的烷基亚胺醚，即B为上述和R.sup.4 =OR.sup.5的公式I化合物；（2）用式为HNR.sup.6 R.sup.7的胺处理步骤（1）的产物，然后用矿酸处理，形成B为上述和R.sup.4 =NR.sup.6 R.sup.7的公式I化合物；（III.）并且如果希望制备A为--CH.dbd.CH--的公式I的化合物，另外对（I.）中的程序制备的产物进行以下步骤：（1）用异丙基二异丙胺处理1,2饱和化合物，形成相应的烯醇负离子；（2）用二苯基二硫处理步骤（1）的烯醇负离子，形成相应的α-苯硫化合物；（3）氧化步骤（2）的产物，形成相应的亚砜化合物；（4）加热步骤（3）的产物，形成A为--CH.dbd.CH--的公式I化合物。
• Multicomponent synthesis of 4,4-dimethyl sterol analogues and their effect on eukaryotic cells
  作者：Fernando Alonso、Adriana M. Cirigliano、María Eugenia Dávola、Gabriela M. Cabrera、Guadalupe E. García Liñares、Carlos Labriola、Andrea A. Barquero、Javier A. Ramírez

  DOI：10.1016/j.steroids.2014.03.002

  日期：2014.6

  Most sterols, such as cholesterol and ergosterol, become functional only after the removal of the two methyl groups at C-4 from their biosynthetic precursors. Nevertheless, some findings suggest that 4,4-dimethyl sterols might be involved in specific physiological processes. In this paper we present the synthesis of a collection of analogues of 4,4-dimethyl sterols with a diamide side chain and a preliminary

  大多数固醇，例如胆固醇和麦角固醇，只有在从其生物合成前体中除去C-4处的两个甲基后，才能发挥功能。然而，一些发现表明4，4-二甲基固醇可能参与特定的生理过程。在本文中，我们介绍了带有二酰胺侧链的4，4-二甲基固醇类似物的合成及其对所选生物系统的体外活性的初步分析。合成的关键步骤涉及Ugi缩合反应，这是一种通用的多组分反应。一些新化合物显示出抗真菌和细胞毒性的活性。
• Selective reduction of 3-keto group in steroidal ketoaldehydes
  作者：M.Paglialunga Paradisi、G.Pagani Zecchini

  DOI：10.1016/0040-4020(82)80258-5

  日期：1982.1

  Convenient preparation of some steroidal 3-hydroxyaldehydes from corresponding 3-ketoaldehydes was achieved by protection of the aldehyde group with t-butylamine followed by in situ reduction of the keto group with Li (t-BuO)3AlH. Final cleavage of hydroxyaldimine was accomplished by eluting the reduction mixture on basic alumina.

  通过用叔丁胺保护醛基，然后用Li（t- BuO）3 AlH原位还原酮基，可以从相应的3-酮醛方便地制备某些甾族3-羟基醛。通过将还原混合物在碱性氧化铝上洗脱，完成了羟醛的最终裂解。
• Azasteroids as inhibitors of rat prostatic 5.alpha.-reductase
  作者：Gary H. Rasmusson、Glenn F. Reynolds、Torleif Utne、Ronald B. Jobson、Raymond L. Primka、Charles Berman、Jerry R. Brooks

  DOI：10.1021/jm00378a028

  日期：1984.12

  were prepared from 3-keto-delta 4-precursors by oxidative (O3 or NaIO4-KMnO4) A-ring cleavage followed, in turn, by ring closure with an amine and hydrogenation over platinum catalyst. Other A-ring azasteroids were made by Beckmann rearrangement of oximes of 2-oxo-A-nor, 3-oxo- and 4-oxo-5 alpha-androstanes. An A-nor-2-oxo-3-azasteroid was prepared by oxidative decarbonylation of a precursor 2,3-dioxo-4-azasteroid

  已经制备了一系列A环杂环类固醇，并在体外测试了其对大鼠前列腺类固醇5α-还原酶的抑制作用。发现一组17个β-取代的4-甲基-4-氮杂-5α-雄甾烷-3-酮具有惊人的高抑制活性。这些化合物由3-酮-δ4前体通过氧化（O3或NaIO4-KMnO4）A环裂解，然后用胺闭环并在铂催化剂上氢化而制得。其他的A环氮杂甾类化合物是通过贝克曼重排2-oxo-A-nor，3-oxo-和4-oxo-5α-雄甾烷酮的肟制得的。通过用间氯过苯甲酸将前体2,3-二氧代-4-氮杂甾族化合物氧化脱羰制备A-正-2-氧代-3-氮杂甾族化合物。4-氮杂类固醇的A环修饰包括δ1-不饱和键，2-和4-取代基以及3-羰基取代基。
• Steroid derivatives for the treatment of prostatic hypertrophy their
  申请人：Sankyo Company, Limited

  公开号：US05536714A1

  公开（公告）日：1996-07-16

  The invention includes compounds of formula (I): ##STR1## in which R.sup.1 is hydrogen, alkyl, aryl-substituted alkyl or aromatic heterocyclic-substituted alkyl; R.sup.2 is aryl-substituted alkyl, aromatic heterocyclic-substituted alkyl or diarylamino; and R.sup.3 is carboxy or a group of formula --CONHSO.sub.2 R.sup.4 wherein R.sup.4 is alkyl; and pharmaceutically acceptable salts and esters of the compounds. The compounds have valuable 5.alpha.-reductase inhibitory activity and can thus be used for the treatment and prophylaxis of, inter alia, prostatic hypertrophy as well as other disorders arising from excess levels of 5.alpha.-dihydro-testosterone.

  该发明包括式(I)的化合物：##STR1##其中R.sup.1是氢，烷基，芳基取代的烷基或芳香杂环基取代的烷基；R.sup.2是芳基取代的烷基，芳香杂环基取代的烷基或二芳基胺基；R.sup.3是羧基或具有式--CONHSO.sub.2 R.sup.4的基团，其中R.sup.4是烷基；以及该化合物的药用可接受盐和酯。这些化合物具有有价值的5α-还原酶抑制活性，因此可用于治疗和预防前列腺肥大等疾病，以及由于5α-二氢睾酮水平过高而引起的其他疾病。