21-chloropregna-16α-methyl-1,4,9(11)-triene-3,20-dione | 151265-34-8

• 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: 21-chloropregna-16α-methyl-1,4,9(11)-triene-3,20-dione
• 英文别名: 21-Chloro-16alpha-methyl-pregna-1,4,9(11)-triene-3-20-dione；(8S,10S,13S,14S,16R,17S)-17-(2-chloroacetyl)-10,13,16-trimethyl-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one
• CAS: 151265-34-8
• 化学式: C₂₂H₂₇ClO₂
• 分子量: 358.908
• InChiKey: NYGQBDLOGUDXAI-YYSFRLGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  21-chloropregna-16α-methyl-1,4,9(11)-triene-3,20-dione 、 2,6-dipyrrolidinyl-4-(1-piperazinyl)-<2,4,6-¹³C3-1,3-¹⁵N2>pyrimidine 在 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 5.0h， 生成 (8S,10S,13S,14S,16R,17S)-17-[2-[4-(2,6-dipyrrolidin-1-yl(2,4,6-13C3,1,3-15N2)pyrimidin-4-yl)piperazin-1-yl]acetyl]-10,13,16-trimethyl-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  Synthesis of radioactive and stable isotope labeled tirilazad mesylate

  摘要：

  Tirilazad美克酸盐，21-[4-(2,6-二（1-吡咯烷基）-4-嘧啶基）-1-哌嗪基]-16α-甲基-孕-1,4,9(11)-三烯-3,20-二酮单甲烷磺酸盐，是一种有效的脂质过氧化抑制剂，能够抑制由创伤或缺血引起的组织损伤进展。已经合成了几种同位素标记的该化合物用于进行该实验药物的体外和体内代谢转化。这些标记包括在分子类固醇部分的16α-甲基基团处用碳-14标记，或在嘧啶环的C-2位置；也包括在类固醇的16α-甲基基团处用氘标记，以及在C-2、C-4和C-6处用碳-13标记，和在嘧啶环的N-1与N-3处用氮-15标记。

  DOI：

  10.1002/jlcr.2580341208
• 作为产物：
  描述：

  16α-methyl-21-hydroxypregna-1,4,9(11)-triene-3,20-dione 在 (氯亚甲基)二甲基氯化铵 、 水 作用下， 生成 21-chloropregna-16α-methyl-1,4,9(11)-triene-3,20-dione
  参考文献：
  名称：

  An Effective Method for the Preparation of 21-Chlorosteroids Using the Vilsmeier Reagent

  摘要：

  A simple procedure for the conversion of 21-steroidal alcohols to the corresponding 21-chlorides using the Vilsmeier reagent is described.

  DOI：

  10.1080/00397919308018615

文献信息

• Steroids, their use as medicaments, their preparation process, the intermediates of this process and the compositions containing them
  申请人：Hoechst Marion Roussel

  公开号：US20020002155A1

  公开（公告）日：2002-01-03

  The subject of the invention is the products of formula (I): 1 in which either R 1 represents halogen, hydroxyl, (C 1 -C 8 ) alkyloxy or (C 1 -C 12 ) acyloxy, and R 2 represents halogen or hydrogen, or R 1 and R 2 form together a double bond, Z is chosen from optionally substituted (C 1 -C 8 ) alkylthio, optionally substituted arylthio, (C 1 -C 8 ) alkyloxy, halogen, cyano, mercapto, thiocyanato and (CH 2 ) 0-1 —CO 2 H, optionally esterified, Y represents hydrogen or methyl, the dotted line in position 1-2 or 5-6 optionally representing a second bond, as well as their addition salts, their preparation process, the intermediates of this process and the pharmaceutical compositions containing them.

  本发明的主题是公式（I）的产物：1，其中R1表示卤素，羟基，（C1-C8）烷氧基或（C1-C12）酰氧基，R2表示卤素或氢，或者R1和R2一起形成双键，Z选择自可选取代的（C1-C8）烷硫基，可选取代的芳基硫基，（C1-C8）烷氧基，卤素，氰基，巯基，硫氰酸根和（CH2）0-1-CO2H，可选酯化，Y表示氢或甲基，位置1-2或5-6的点线可选地表示第二个键，以及它们的加成盐，制备过程，该过程的中间体和含有它们的药物组合物。
• Pregnane derivatives with no alpha-17 substitutent, their medicinal use, manufacturing method and its intermediaries and related compounds
  申请人：Aventis Pharma S.A.

  公开号：US06274572B1

  公开（公告）日：2001-08-14

  The subject of the invention is the products of formula (I): in which either R1 represents halogen, hydroxyl, (C1-C8) alkyloxy or (C1-C12) acyloxy, and R2 represents halogen or hydrogen, or R1 and R2 form together a double bond, Z is chosen from optionally substituted (C1-C8) alkylthio, optionally substituted arylthio, (C1-C8) alkyloxy, halogen, cyano, mercapto, thiocyanato and (CH2)0-1—CO2H, optionally esterified, Y represents hydrogen or methyl, the dotted line in position 1-2 or 5-6 optionally representing a second bond, as well as their addition salts, their preparation process, the intermediates of this process and the pharmaceutical compositions containing them.

  本发明的主题是公式（I）的产物：其中，R1代表卤素、羟基、（C1-C8）烷氧基或（C1-C12）酰氧基，R2代表卤素或氢，或者R1和R2共同形成双键，Z选择自可选取取代的（C1-C8）烷基硫醚、可选取取代的芳基硫醚、（C1-C8）烷氧基、卤素、氰基、巯基、硫氰酸基和（CH2）0-1—CO2H，可选酯化，Y代表氢或甲基，位置1-2或5-6的虚线可选择表示第二个键，以及它们的加成盐、制备方法、该方法的中间体和含有它们的药物组合物。
• US6274572B1
  申请人：——

  公开号：US6274572B1

  公开（公告）日：2001-08-14
• US6492536B2
  申请人：——

  公开号：US6492536B2

  公开（公告）日：2002-12-10
• Synthesis of radioactive and stable isotope labeled tirilazad mesylate
  作者：W. T. Stolle、J. A. Easter、E. H. Chew、J. P. McGrath、J. R. Palmer、R. S. P. Hsi

  DOI：10.1002/jlcr.2580341208

  日期：1994.12

  Tirilazad mesylate, 21-[4-(2,6-di-1-pyrrolidinyl-4-pyrimidinyl)-1-piperazinyl]-16α-methyl-pregna-1,4,9(11)-triene-3,20-dione monomethanesulfonate, is a potent lipid peroxidation inhibitor capable of suppressing progression of tissue damage caused by trauma or ischemia. Several isotopically labeled versions of the compound have been synthesized for conducting in vitro and in vivo metabolic transformations of this experimental drug. These include labeling with carbon-14 at the 16α-methyl group of the steroid portion of the molecule, or at the C-2 position of the pyrimidine ring; also with deuterium at the steroid 16α-methyl group, and/or with carbon-13 at C-2, C-4, and C-6, and with nitrogen-15 at N-1 and N-3 of the pyrimidine ring.

  Tirilazad美克酸盐，21-[4-(2,6-二（1-吡咯烷基）-4-嘧啶基）-1-哌嗪基]-16α-甲基-孕-1,4,9(11)-三烯-3,20-二酮单甲烷磺酸盐，是一种有效的脂质过氧化抑制剂，能够抑制由创伤或缺血引起的组织损伤进展。已经合成了几种同位素标记的该化合物用于进行该实验药物的体外和体内代谢转化。这些标记包括在分子类固醇部分的16α-甲基基团处用碳-14标记，或在嘧啶环的C-2位置；也包括在类固醇的16α-甲基基团处用氘标记，以及在C-2、C-4和C-6处用碳-13标记，和在嘧啶环的N-1与N-3处用氮-15标记。