4-[10,11-二氢-8-(甲硫基)二苯并[b,f]硫杂卓-10-基]-1-哌嗪丙醇 | 29604-16-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫平类
• 中文名称: 4-[10,11-二氢-8-(甲硫基)二苯并[b,f]硫杂卓-10-基]-1-哌嗪丙醇
• 英文名称: 10-<4-(3-hydroxypropyl)piperazino>-8-methylthio-10,11-dihydrodibenzothiepin
• 英文别名: oxyprothepine；Oxyprothepin；3-[4-(8-methylsulfanyl-10,11-dihydro-dibenzo[b,f]thiepin-10-yl)-piperazin-1-yl]-propan-1-ol；8-methylthio-10-[4-(3-hydroxypropyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepin；3-[4-(3-methylsulfanyl-5,6-dihydrobenzo[b][1]benzothiepin-5-yl)piperazin-1-yl]propan-1-ol
• CAS: 29604-16-8
• 化学式: C₂₂H₂₈N₂OS₂
• 分子量: 400.609
• InChiKey: HQOCWPHRUQRXEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  77.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[10,11-二氢-8-(甲硫基)二苯并[b,f]硫杂卓-10-基]-1-哌嗪丙醇 生成 1,4-bis(8-methylthio-10,11-dihydrodibenzothiepin-10-yl)piperazine
  参考文献：
  名称：

  JILEK, J.;POMYKACEK, J.;PROSEK, Z.;HOLUBEK, J.;SVATEK, E.;METYSOVA, J.;DL+, COLLECT. CZECH. CHEM. COMMUN., 1983, 48, N 3, 906-927

  摘要：

  DOI：
• 作为产物：
  描述：

  oxyprothepine-8-sulfoxide 在 cytoplasmic sulfoxide reductase 、 还原型辅酶II(NADPH)四钠盐 作用下， 生成 4-[10,11-二氢-8-(甲硫基)二苯并[b,f]硫杂卓-10-基]-1-哌嗪丙醇
  参考文献：
  名称：

  Paulikova; Helia, Pharmazie, 1994, vol. 49, # 7, p. 531 - 532

  摘要：

  DOI：

文献信息

• Neuroleptics of the 8-methylthio-10-piperazino-10,11-dihydrodibenzo[b,f]thiepin series: New compounds and new procedures
  作者：Jiří Jílek、Josef Pomykáček、Antonín Dlabač、Marie Bartošová、Miroslav Protiva

  DOI：10.1135/cccc19800504

  日期：——

  Heating of 8-methylthiodibenzo[b,f]thiepin-10(11H)-one with mono-p-toluenesulfonates of 1-methylpiperazine and piperazine in vacuo led in good yields to the enamines IX-XI, the first of which was reduced with zinc and acetic acid to the base I (methiothepin). The ester III(oxyprothepindecanoate) was obtained by reaction of the amino alcohol II (oxyprothepin) with decanoic acid in the presence of N,N'-carbonyldiimidazole and by substitution of 10-chloro-8-methylthio-10,11-dihydrobenzo[b,f]thiepin with 1-(3-decanoyloxypropyl)piperazine. The substitution reaction of the same chloro compound with piperazine gave two stereoisomeric 1,4-disubstituted piperazines V. Reaction of the amino alcohol II with octyl isocyanate afforded the carbamate VI, an isoster of oxyprothepin decanoate (III). This substance showed in the test of antiapomorphine activity in dogs the properties of a long-acting antiemetic. Two new potential metabolites (XII, XIII) of compounds I-III were synthesized and new pharmacological data are given for two further potential metabolites (XIV, XV) of oxyprothepin (II).

  将8-甲硫基二苯并[b,f]噻吩-10(11H)-酮与1-甲基哌嗪和哌嗪的单-p-甲苯磺酸酯在真空中加热，产率良好地得到烯胺IX-XI，其中第一个被还原为基本物质I（甲硫噻吩）的烯胺被锌和乙酸处理。通过氨基醇II（氧丙硫噻吩）与癸酸在N,N'-碳酰二咪唑存在下反应，并通过用1-(3-癸酰氧丙基)哌嗪替代10-氯-8-甲硫基-10,11-二氢二苯并[b,f]噻吩制得酯III（氧丙硫噻吩癸酸酯）。同一氯化合物与哌嗪的取代反应得到两个立体异构体的1,4-二取代哌嗪V。氨基醇II与辛基异氰酸酯反应得到氨基甲酸酯VI，是氧丙硫噻吩癸酸酯（III）的同分异构体。该物质在狗的抗阿波吗啡活性测试中表现出长效抗恶心的特性。合成了化合物I-III的两种新潜在代谢物（XII, XIII），并为氧丙硫噻吩（II）的另外两种潜在代谢物（XIV, XV）提供了新的药理数据。
• Fatty acid esters of 8-substituted
  申请人：SPOFA, Sdruzeni podniku pro zdravotnickou vyrobu

  公开号：US03985750A1

  公开（公告）日：1976-10-12

  Fatty acid esters of 8-substituted 10-[4-(hydroxyalkyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepins and oxepins having the formula ##SPC1## In which X is a sulfur or oxygen atom, R.sup.1 is a hydrogen, chloro, or trifluoromethyl radical, a lower alkyl radical having at most 5 carbon atoms, or a cycloalkyl radical having at least 3 and at most 8 carbon atoms, or an alkoxy or alkylthio radical the alkyl moiety of which has at most 4 carbon atoms, R.sup.2 is an alkyl radical having at least 5 and at most 17 carbon atoms, and n is 2, 3, or 4, and their salts with pharmaceutically acceptable inorganic and organic acids. The compounds have a high degree of neuroleptic activity and retain this activity for long periods after administration. Related fatty acid esters of 8-substituted 10-[4-(hydroxyalkyl)-piperazino]dibenzo[b,f]thiepins and oxepins having the formula ##SPC2## And fatty acid esters of 8-substituted 4-[4-(hydroxyalkyl)piperazino]thieno[2,3-b]-1-benzothiepins and oxepins having the formula ##SPC3## In which formulae X, R.sup.1, R.sup.2 and n each have the foregoing significance, are also included herein.

  公式为##SPC1##的8-取代的10-[4-(羟基烷基)哌嗪基]-10,11-二氢二苯并[b,f]噻吩和氧杂环的脂肪酸酯，其中X为硫或氧原子，R1为氢、氯或三氟甲基基团、最多有5个碳原子的低碳基基团、至少有3个碳原子且最多有8个碳原子的环烷基基团，或烷氧基或烷硫基基团，其烷基部分最多有4个碳原子，R2为至少有5个碳原子且最多有17个碳原子的烷基基团，n为2、3或4，并且它们与药学上可接受的无机和有机酸的盐。这些化合物具有高度的神经抑制活性，并在给药后长时间保持这种活性。本文还包括公式为##SPC2##的8-取代的10-[4-(羟基烷基)哌嗪基]二苯并[b,f]噻吩和氧杂环的脂肪酸酯以及公式为##SPC3##的8-取代的4-[4-(羟基烷基)哌嗪基]噻吩[2,3-b]-1-苯并噻吩和氧杂环的脂肪酸酯，其中公式中的X、R1、R2和n具有上述意义。
• Jilek,Jiri; Pomykacek, Josef; Prosek, Zdenek, Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 3, p. 906 - 927
  作者：Jilek,Jiri、Pomykacek, Josef、Prosek, Zdenek、Holubek, Jiri、Svatek, Emil、et al

  DOI：——

  日期：——
• JILEK J.; POMYKACEK J.; DLABAC A.; BARTOSOVA M., COLLECT. CZECH. CHEM. COMMUN., 1980, 45, NO 2, 504-516
  作者：JILEK J.、 POMYKACEK J.、 DLABAC A.、 BARTOSOVA M.

  DOI：——

  日期：——
• PROTIVA, M.;JILEK, J.;DLABAC, A.
  作者：PROTIVA, M.、JILEK, J.、DLABAC, A.

  DOI：——

  日期：——