4-nitroandrost-4-ene-3,17-dione | 173285-58-0

• 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: 4-nitroandrost-4-ene-3,17-dione
• 英文别名: (8R,9S,10R,13S,14S)-10,13-dimethyl-4-nitro-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 173285-58-0
• 化学式: C₁₉H₂₅NO₄
• 分子量: 331.412
• InChiKey: JPMDSLNZBGWFSP-KZQROQTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  17β-hydroxy-4-nitroandrost-4-en-3-one 、 Jones' reagent 、 甲醇 在 silica gel 、 acetone hexane 作用下， 以 丙酮 为溶剂， 以to give 4-nitroandrost-4-ene-3,17-dione, m.p. 205-205.5° C. dec.(acetone-hexane)的产率得到4-nitroandrost-4-ene-3,17-dione
  参考文献：
  名称：

  Certain 3-ketosteroids used to inhibit steroid 5.alpha.-reductase

  摘要：

  该发明揭示了以下公式的3-酮类固醇，用于抑制类固醇5α-还原酶：##STR1## 其中R为OH，C.sub.1-C.sub.6烷酰基，C.sub.1-C.sub.6烷氧基，C.sub.1-C.sub.4烷醇，COCH.sub.2OH，CO.sub.2H，CONR.sub.7R.sub.8，环丙氧基，乙酰硫代烷基，环戊氨基，2-2-二甲基二氧杂环戊烷-4-基，1,2-二羟乙基和C.sub.1-4烷硫醇；R.sub.1为氢，羟基或C.sub.1-6烷基；R.sub.1和R.sub.2可以共同表示.dbd.O，即与第17碳双键的氧原子；R.sub.2，R.sub.3和R.sub.4各自独立地是氢或C.sub.1-6烷基；R.sub.5和R.sub.6各自独立地是氢或羟基；R.sub.5和R.sub.6可以共同表示.dbd.O，即与第11碳双键的氧原子；R.sub.7为氢或C.sub.1-8烷基；R.sub.8为C.sub.1-8烷基；但是，当R为OH时，R.sub.1为氢；而且，当R.sub.5为OH时，R.sub.6为氢。

  公开号：

  US05869475A1

文献信息

• Process for the preparation of 4-amino- 4-3-ketosteroids via 4-nitro-
  申请人：Merrell Pharmaceuticals Inc.

  公开号：US05750744A1

  公开（公告）日：1998-05-12

  The present invention provides 4-nitro-.DELTA..sup.4 -3-ketosteroids, their use as steroid C.sub.17-20 lyase and 5.alpha.-reductase inhibitors and to a novel process for preparing a compound of the formula: ##STR1## comprising sequentially: a) reacting a starting compound of the formula ##STR2## with an effective amount of a strong base at an elevated or suitable temperature for a time sufficient to create the corresponding thermodynamic dienolate, followed by addition of a neutral nitrating agent to produce the 4-nitro-steroid; and then; b) reacting the 4-nitrosteroid with a suitable reducing agent.

  本发明提供4-硝基-.DELTA..sup.4-3-酮类固醇，其用作类固醇C.sub.17-20裂解酶和5α-还原酶抑制剂，并提供了一种制备式化合物的新方法：##STR1## 顺序包括：a)在升高或适宜温度下，使用有效量的强碱与式化合物##STR2##反应，以产生相应的热力学二烯酸盐，然后加入中性硝化剂以产生4-硝基类固醇;然后;b)使用适当的还原剂与4-硝基类固醇反应。
• Process for the preparation of 4-amino-.DELTA..sup.4 -3-ketosteroids via
  申请人：Merrell Pharmaceuticals Inc.

  公开号：US05965550A1

  公开（公告）日：1999-10-12

  The invention discloses 3-ketosteroids of the following formula used to inhibit steroid C.sub.17-20 lyase: ##STR1## wherein R is OH, C.sub.1 -C.sub.6 alkanoyl, C.sub.1 -C.sub.6 alkanoyloxy, C.sub.1 -C.sub.4 alkanol, COCH.sub.2 OH, CO.sub.2 H, CONR.sub.7 R.sub.8, cyclopropyloxy, cyclopropylamino, acetylthioalkane, 2,2-dimethyldioxolan4-yl, 1,2-dihydroxyethyl and C.sub.1-4 alkylthiol; R.sub.1 is hydrogen, hydroxy or C.sub.1-6 alkyl; R and R.sub.1 together may indicate .dbd.O, that is an oxygen double bonded to the 17 carbon; R.sub.2, R.sub.3, and R.sub.4 are each independently hydrogen or C.sub.1 -C.sub.6 alkyl; R.sub.5 and R.sub.6 are each independently hydrogen or OH; R.sub.5 and R.sub.6 together may indicate .dbd.O, that is an oxygen double bonded to the 11 carbon; R.sub.7 is hydrogen or C.sub.1 -C.sub.8 alkyl; R.sub.8 is C.sub.1 -C.sub.8 alkyl; and with the proviso that, when R is OH, then R.sub.1 is hydrogen; and with the proviso that, when R.sub.5 is OH, then R.sub.6 is hydrogen.

  本发明揭示了以下式子的3-酮类固醇，用于抑制类固醇C.sub.17-20裂解酶：##STR1## 其中R为OH，C.sub.1-C.sub.6烷酰基，C.sub.1-C.sub.6烷酰氧基，C.sub.1-C.sub.4烷醇，COCH.sub.2OH，CO.sub.2H，CONR.sub.7R.sub.8，环丙氧基，环丙氨基，乙酰硫代烷基，2,2-二甲基二氧杂环己基，1,2-二羟乙基和C.sub.1-4烷基硫醇; R.sub.1为氢，羟基或C.sub.1-6烷基; R和R.sub.1一起可以表示.dbd.O，即与17碳形成双键的氧原子; R.sub.2、R.sub.3和R.sub.4各自独立地为氢或C.sub.1-C.sub.6烷基; R.sub.5和R.sub.6各自独立地为氢或OH; R.sub.5和R.sub.6一起可以表示.dbd.O，即与11碳形成双键的氧原子; R.sub.7为氢或C.sub.1-C.sub.8烷基; R.sub.8为C.sub.1-C.sub.8烷基; 前提是，当R为OH时，R.sub.1为氢; 前提是，当R.sub.5为OH时，R.sub.6为氢。
• Process for the preparation of 4-amino-.DELTA.4-3-ketosteroids via
  申请人：Merrell Pharmaceuticals Inc.

  公开号：US05990328A1

  公开（公告）日：1999-11-23

  The present invention provides 4-nitro-.DELTA..sup.4 -3-ketosteroids, their use as steroid C.sub.17-20 lyase and 5.alpha.-reductase inhibitors and to a novel process for preparing a compound of the formula: ##STR1## comprising sequentially: a) reacting a starting compound of the formula ##STR2## with an effective amount of a strong base at an elevated or suitable temperature for a time sufficient to create the corresponding thermodynamic dienolate, followed by addition of a neutral nitrating agent to produce the 4-nitrosteroid; and then; b) reacting the 4-nitrosteroid with a suitable reducing agent.

  本发明提供了4-硝基-.DELTA..sup.4 -3-酮类固醇化合物，其用作类固醇C.sub.17-20裂解酶和5α-还原酶抑制剂，以及一种新的制备公式为：##STR1##的化合物的方法，包括顺序地：a)在升高或适当温度下，反应公式为##STR2##的起始化合物与有效量的强碱，足以产生相应的热力学二烯醇负离子，然后添加中性硝化剂以产生4-硝基类固醇；然后；b)用适当的还原剂反应4-硝基类固醇。
• PROCESS FOR THE PREPARATION OF 4-AMINO-DELTA 4-3-KETOSTEROIDS VIA 4-NITRO-DELTA 4-3-KETOSTEROIDS
  申请人：MERRELL PHARMACEUTICALS INC.

  公开号：EP0758340B1

  公开（公告）日：1999-01-07
• US5750744A
  申请人：——

  公开号：US5750744A

  公开（公告）日：1998-05-12