17α-<(Z)-2-iodoethenyl>androst-4-en-17β-ol-3-one | 98256-42-9

• 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: 17α-<(Z)-2-iodoethenyl>androst-4-en-17β-ol-3-one
• 英文别名: 17α-((Z)-2-iodoethenyl)androst-4-en-17β-ol-3-one；17β-hydroxy-17α-(Z-2-iodovinyl)-4-androsten-3-one；(8R,9S,10R,13S,14S,17R)-17-hydroxy-17-[(Z)-2-iodoethenyl]-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 98256-42-9
• 化学式: C₂₁H₂₉IO₂
• 分子量: 440.365
• InChiKey: PPYYSWDWXBNTNL-HSNNQIHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  17α-<(Z)-2-iodoethenyl>androst-4-en-17β-ol-3-one 在 四氯苯醌 作用下， 以 叔丁醇 为溶剂， 反应 18.0h， 以55%的产率得到17α-<(Z)-2-iodoethenyl>androsta-4,6-dien-17β-ol-3-one
  参考文献：
  名称：

  Preparation of 17α-iodoethynylandrosta- and 17α-(2-iodoethenyl) androsta-4,6-dien-17β-ol-3-ones as active site-directed photoaffinity ligands for androgen-binding proteins

  摘要：

  Unsaturated analogues of androst-4-en-17 beta-ol-3-one, each with a 17 alpha-iodoethynyl or 17 alpha-(2-iodoethenyl) substituent, were prepared, and their relative binding affinities (RBAs) for androgen-binding protein (ABP) were compared with those of 5 alpha-androstan-17 beta-ol-3-one, androst-4-en-17 beta-ol-3-one, androsta-4,6-dien-17 beta-ol-3-one, and androsta-1,4,6-trien-17 beta-ol-3-one. These binding studies indicate that the iodine[125I] analogues of 17 alpha-iodoethynyl and 17 alpha-[(E)-2-iodoethenyl] derivatives of androsta-4,6-dien-17 beta-ol-3-one and androsta-1,4,6-trien-17 beta-ol-3-one will have RBAs at least twice as great as that of 5 alpha-androstan-17 beta-ol-3-one. They can be prepared from 17 alpha-ethynylandrosta-4-en-17 beta-ol-3-one, the final synthetic step using N-[125I]iodosuccinimide, and are potential radioiodinated, active site-directed photoaffinity ligands for ABP and testosterone-binding globulin.

  DOI：

  10.1016/0039-128x(92)90027-7
• 作为产物：
  描述：

  17α-ethynyl-17β-hydroxy-5-androsten-3-one ethylene ketal 在 N-碘代丁二酰亚胺 、 2,4,6-三异丙基苯磺酰基肼 、 草酸 、 silver nitrate 、 三乙胺 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 6.0h， 生成 17α-<(Z)-2-iodoethenyl>androst-4-en-17β-ol-3-one
  参考文献：
  名称：

  Preparation of 17α-iodoethynylandrosta- and 17α-(2-iodoethenyl) androsta-4,6-dien-17β-ol-3-ones as active site-directed photoaffinity ligands for androgen-binding proteins

  摘要：

  Unsaturated analogues of androst-4-en-17 beta-ol-3-one, each with a 17 alpha-iodoethynyl or 17 alpha-(2-iodoethenyl) substituent, were prepared, and their relative binding affinities (RBAs) for androgen-binding protein (ABP) were compared with those of 5 alpha-androstan-17 beta-ol-3-one, androst-4-en-17 beta-ol-3-one, androsta-4,6-dien-17 beta-ol-3-one, and androsta-1,4,6-trien-17 beta-ol-3-one. These binding studies indicate that the iodine[125I] analogues of 17 alpha-iodoethynyl and 17 alpha-[(E)-2-iodoethenyl] derivatives of androsta-4,6-dien-17 beta-ol-3-one and androsta-1,4,6-trien-17 beta-ol-3-one will have RBAs at least twice as great as that of 5 alpha-androstan-17 beta-ol-3-one. They can be prepared from 17 alpha-ethynylandrosta-4-en-17 beta-ol-3-one, the final synthetic step using N-[125I]iodosuccinimide, and are potential radioiodinated, active site-directed photoaffinity ligands for ABP and testosterone-binding globulin.

  DOI：

  10.1016/0039-128x(92)90027-7

文献信息

• Estrane and androstane derivatives, process for producing them and
  申请人：Schering Aktiengesellschaft

  公开号：US04945064A1

  公开（公告）日：1990-07-31

  Estrane and androstane derivatives of formula I ##STR1## wherein X is bromine, iodine, triphenyltin or trialkyltin of 1 to 6 carbon atoms per alkyl radical, Y represents two hydrogen atoms or methylene, Z represents two hydrogen atoms, oxo or alkylenedioxy of 2 to 6 carbon atoms and V is ethylene, vinylene, 1,3-propylene or cyclopropylene, R.sub.1 is hydrogen or a hydrocarbon radical of up to 8 hydrocarbon atoms, optionally interrupted by an oxa group or substituted by an oxo group, R.sub.2 is methyl or ethyl, R.sub.3 and R.sub.4 represent a carbon-carbon bond or R.sub.3 is hydrogen and R.sub.4 is hydrogen or methyl, .DELTA.symbolizes a 4(5)-double bond if Z signifies two hydrogen atoms or an oxo group; or a 5(6)-double bond or, for the estrane derivatives of formula I, also a 5(10)-double bond, if Z is alkylenedioxy, are pharmacologically effective substances or intermediates for preparation thereof.

  ESTrane和androSTa href=https://www.molaid.com/MS_164855 target="_blank">TAne的衍生物的化学式为I ##STR1## 其中X是溴、碘、三苯基锡或1至6个碳原子的烷基基团的三烷基锡，Y代表两个氢原子或亚甲基，Z代表两个氢原子、氧化物或2至6个碳原子的烷基二氧基，V是乙烯、乙烯基、1,3-丙烯或环丙烯，R.sub.1是氢或最多8个碳原子的烃基，可由氧杂环截断或被氧化物基取代，R.sub.2是甲基或乙基，R.sub.3和R.sub.4代表碳-碳键或R.sub.3是氢，R.sub.4是氢或甲基，如果Z表示两个氢原子或氧化物基，则.DELTA.表示4(5)-双键；如果Z是烷基二氧基，则表示5(6)-双键或对于化学式I的eSTrane衍生物，也表示5(10)-双键，这些化合物或其制备中间体具有药理学上的有效性。
• Estran- und Androstan-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Präparate
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0137434B1

  公开（公告）日：1992-01-29
• US4885117A
  申请人：——

  公开号：US4885117A

  公开（公告）日：1989-12-05
• US4945064A
  申请人：——

  公开号：US4945064A

  公开（公告）日：1990-07-31
• [EN] PROCESS FOR PRODUCING (Z)-17 alpha -HALOGENVINYLSTEROIDS
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：WO1988001276A2

  公开（公告）日：1988-02-25

  (EN) A process for producing (Z)-17$g(a)-halogenvinylsteroids having general formula (I), in which ..... represents a simple or a double bond, V represents a carbon-carbon bond or a methyl group, R1 is a hydrogen atom or a methyl group, X is an atom of chlorine, bromine or iodine and A represents the rest of the steroid molecule. The process consists of hydrating with diimide a 17$g(a)-halogenethinylsteroid having formula (II), in which ....., V, R1, X and A have the above meaning.(FR) Un procédé sert à produire des stéroïdes de (Z)-17$g(a)-vinyle halogéné ayant la formule générale (I), dans laquelle ..... représente une liaison simple ou double, V représente une liaison carbone-carbone ou un groupe méthyle, R1 est un atome d'hydrogèneou un groupe méthyle, X est un atome de chlore, de brome ou de iode et A représente le reste de la molécule stéroïde. Le procédé comprend l'hydratation avec un diimide d'un stéroïde de 17$g(a)-éthinyle halogéné ayant la formule (II), dans laquelle ....., V, R1, X et A ont la signification décrite ci-dessus.