4-benzyl-1-hexanoylpiperazine | 289476-05-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-benzyl-1-hexanoylpiperazine
• 英文别名: 1-(4-Benzylpiperazin-1-yl)hexan-1-one
• CAS: 289476-05-7
• 化学式: C₁₇H₂₆N₂O
• 分子量: 274.406
• InChiKey: HBTWPJIVPQSBCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-benzyl-1-hexanoylpiperazine 在 10percent Pd/C 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 1-己酰基哌嗪
  参考文献：
  名称：

  Molecular Simplification of 1,4-Diazabicyclo[4.3.0]nonan-9-ones Gives Piperazine Derivatives That Maintain High Nootropic Activity

  摘要：

  Several 4-substituted 1-acylpiperazines, obtained by molecular simplification of 4-substituted 1,4-diazabicyclo[4.3.0]nonan-9-ones, have been synthesized and tested in vivo on the mouse passive avoidance test, to evaluate their nootropic activity. The results show that, apparently, an N-acylpiperazine group can mimic the 2-pyrrolidinone ring of 1,4-diazabicyclo[4.3.0]nonan-9-one, as the compounds of the new series maintain high nootropic activity. Moreover molecular simplification produces more clear-cut structure-activity relationships with respect to the parent series. The mechanism of action also appears to be similar in the two series. In fact, although the molecular mechanism remains to be elucidated, the most potent compound of each class (DM232 and 13, DM235) is able to increase acetylcholine release in rat brain. Piperazine derivatives represent a new class of nootropic drugs with an in vivo pharmacological profile very similar to that of piracetam, showing much higher potency with respect to the reference compound. Among the compounds studied, 13 (DM235) shows outstanding potency, being active at a dose of 0.001 mg kg(-1) sc.

  DOI：

  10.1021/jm000972h
• 作为产物：
  描述：

  1-苄基哌嗪 、 己酰氯 在 三乙胺 作用下， 反应 2.0h， 生成 4-benzyl-1-hexanoylpiperazine
  参考文献：
  名称：

  Molecular Simplification of 1,4-Diazabicyclo[4.3.0]nonan-9-ones Gives Piperazine Derivatives That Maintain High Nootropic Activity

  摘要：

  Several 4-substituted 1-acylpiperazines, obtained by molecular simplification of 4-substituted 1,4-diazabicyclo[4.3.0]nonan-9-ones, have been synthesized and tested in vivo on the mouse passive avoidance test, to evaluate their nootropic activity. The results show that, apparently, an N-acylpiperazine group can mimic the 2-pyrrolidinone ring of 1,4-diazabicyclo[4.3.0]nonan-9-one, as the compounds of the new series maintain high nootropic activity. Moreover molecular simplification produces more clear-cut structure-activity relationships with respect to the parent series. The mechanism of action also appears to be similar in the two series. In fact, although the molecular mechanism remains to be elucidated, the most potent compound of each class (DM232 and 13, DM235) is able to increase acetylcholine release in rat brain. Piperazine derivatives represent a new class of nootropic drugs with an in vivo pharmacological profile very similar to that of piracetam, showing much higher potency with respect to the reference compound. Among the compounds studied, 13 (DM235) shows outstanding potency, being active at a dose of 0.001 mg kg(-1) sc.

  DOI：

  10.1021/jm000972h
• 作为试剂：
  描述：

  1-苄基哌嗪 、 己酰氯 、 三乙胺 在 ice 、 potassium hydrogensulfate 、 碳酸氢钠 、 Brine 、 Sodium sulfate-III 、 二氯甲烷 、 crude material 、 toluene-ethyl acetate 、 4-benzyl-1-hexanoylpiperazine 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以to give 453 mg of colorless oil的产率得到4-benzyl-1-hexanoylpiperazine
  参考文献：
  名称：

  Composition for treatment of tuberculosis

  摘要：

  本发明涉及一种药物组合物，包括式（1）中的化合物，其中R1是可选取代的苯基、可选取代的吡啶基或可选取代的吲哚基；R2是（CH2）n，其中n为0、1、2、3或4；R3是（CH2）mR3A，其中m为0、1、2、3或4，R3A是甲基、异丙基、叔丁基、OCH3、OH、可选取代的苯氧基、C≡CH、C≡N、可选取代的苯基、呋喃基或噻吩基；A是含有X1的环，X1的含义为O、S、NH、N（CH3）或CH2；X2是O、S或NH；以及式（2）中的化合物，其中R4是可选取代的苯基、可选取代的吡啶基、可选取代的吲哚基、—NR7R8；或—NH—N═CH—R9；且取代基R5到R9的含义在说明书中有所说明，特别是乙硫异烟胺。该药物组合物可用于治疗多药耐药性结核病等疾病。

  公开号：

  US08912329B2

文献信息

• COMPOSITION FOR TREATMENT OF TUBERCULOSIS
  申请人：Schoenmakers Ronald

  公开号：US20120101080A1

  公开（公告）日：2012-04-26

  The invention relates to a pharmaceutical composition comprising a compound of formula (1) wherein R 1 is optionally substituted phenyl, optionally substituted pyridyl or optionally substituted indolyl; R 2 is (CH 2 ) n wherein n is 0, 1, 2, 3 or 4; R 3 is (CH 2 ) m R 3A wherein m is 0, 1, 2, 3 or 4, and R 3A is methyl, isopropyl, tert-butyl, OCH 3 , OH, optionally substituted phenoxy, C≡CH, C≡N, optionally substituted phenyl, furanyl or thienyl; A is a ring containing X 1 with the meaning O, S, NH, N(CH 3 ) or CH 2 ; and X 2 is O, S or NH; and a compound of formula (2) wherein R 4 is optionally substituted phenyl, optionally substituted pyridyl, optionally substituted indolyl, —NR 7 R 8 ; or —NH—N═CH—R 9 ; and substituents R 5 to R 9 have the meanings indicated in the description, in particular ethionamide. The pharmaceutical composition is useful, e.g., in the treatment of multidrug-resistant tuberculosis.

  本发明涉及一种药物组合物，其中包含式（1）的化合物，其中R1是可选取代苯基，可选取代吡啶基或可选取代吲哚基；R2是（CH2）n，其中n为0、1、2、3或4；R3是（CH2）mR3A，其中m为0、1、2、3或4，R3A是甲基、异丙基、叔丁基、OCH3、OH、可选取代苯氧基、C≡CH、C≡N、可选取代苯基、呋喃基或噻吩基；A是一个含有X1环，X1的含义是O、S、NH、N(CH3)或CH2；X2是O、S或NH；以及式（2）的化合物，其中R4是可选取代苯基，可选取代吡啶基，可选取代吲哚基，—NR7R8；或—NH—N═CH—R9；和取代基R5至R9在说明书中有所示，特别是乙硫异烟胺。该药物组合物在治疗多药耐药结核病方面具有用途。
• US8912329B2
  申请人：——

  公开号：US8912329B2

  公开（公告）日：2014-12-16
• [EN] COMPOSITION FOR TREATMENT OF TUBERCULOSIS<br/>[FR] COMPOSITION POUR LE TRAITEMENT DE LA TUBERCULOSE
  申请人：BIOVERSYS GMBH

  公开号：WO2010149761A1

  公开（公告）日：2010-12-29

  The invention relates to a pharmaceutical composition comprising a compound of formula (1) wherein R1 is optionally substituted phenyl, optionally substituted pyridyl or optionally substituted indolyl; R2 is (CH2)n wherein n is 0,1,2,3 or 4; R3 is (CH2)m R3A wherein m is 0,1,2,3 or 4, and R3A is methyl, isopropyl, tert-butyl, OCH3, OH, optionally substituted phenoxy, C≡CH, C≡N, optionally substituted phenyl, furanyl or thienyl; A is a ring containing X1 with the meaning O, S, NH, N(CH3) or CH2; and X2 is O, S or NH; and a compound of formula (2) wherein R4 is optionally substituted phenyl, optionally substituted pyridyl, optionally substituted indolyl, -NR7R8; or -NH-N=CH-R9; and substituents R5 to R9 have the meanings indicated in the description, in particular ethionamide. The pharmaceutical composition is useful, e.g., in the treatment of multidrug-resistant tuberculosis.
• Molecular Simplification of 1,4-Diazabicyclo[4.3.0]nonan-9-ones Gives Piperazine Derivatives That Maintain High Nootropic Activity
  作者：Dina Manetti、Carla Ghelardini、Alessandro Bartolini、Silvia Dei、Nicoletta Galeotti、Fulvio Gualtieri、Maria Novella Romanelli、Elisabetta Teodori

  DOI：10.1021/jm000972h

  日期：2000.11.1

  Several 4-substituted 1-acylpiperazines, obtained by molecular simplification of 4-substituted 1,4-diazabicyclo[4.3.0]nonan-9-ones, have been synthesized and tested in vivo on the mouse passive avoidance test, to evaluate their nootropic activity. The results show that, apparently, an N-acylpiperazine group can mimic the 2-pyrrolidinone ring of 1,4-diazabicyclo[4.3.0]nonan-9-one, as the compounds of the new series maintain high nootropic activity. Moreover molecular simplification produces more clear-cut structure-activity relationships with respect to the parent series. The mechanism of action also appears to be similar in the two series. In fact, although the molecular mechanism remains to be elucidated, the most potent compound of each class (DM232 and 13, DM235) is able to increase acetylcholine release in rat brain. Piperazine derivatives represent a new class of nootropic drugs with an in vivo pharmacological profile very similar to that of piracetam, showing much higher potency with respect to the reference compound. Among the compounds studied, 13 (DM235) shows outstanding potency, being active at a dose of 0.001 mg kg(-1) sc.
• Composition for treatment of tuberculosis
  申请人：Schoenmakers Ronald

  公开号：US08912329B2

  公开（公告）日：2014-12-16

  The invention relates to a pharmaceutical composition comprising a compound of formula (1) wherein R1 is optionally substituted phenyl, optionally substituted pyridyl or optionally substituted indolyl; R2 is (CH2)n wherein n is 0, 1, 2, 3 or 4; R3 is (CH2)mR3A wherein m is 0, 1, 2, 3 or 4, and R3A is methyl, isopropyl, tert-butyl, OCH3, OH, optionally substituted phenoxy, C≡CH, C≡N, optionally substituted phenyl, furanyl or thienyl; A is a ring containing X1 with the meaning O, S, NH, N(CH3) or CH2; and X2 is O, S or NH; and a compound of formula (2) wherein R4 is optionally substituted phenyl, optionally substituted pyridyl, optionally substituted indolyl, —NR7R8; or —NH—N═CH—R9; and substituents R5 to R9 have the meanings indicated in the description, in particular ethionamide. The pharmaceutical composition is useful, e.g., in the treatment of multidrug-resistant tuberculosis.

  本发明涉及一种药物组合物，包括式（1）中的化合物，其中R1是可选取代的苯基、可选取代的吡啶基或可选取代的吲哚基；R2是（CH2）n，其中n为0、1、2、3或4；R3是（CH2）mR3A，其中m为0、1、2、3或4，R3A是甲基、异丙基、叔丁基、OCH3、OH、可选取代的苯氧基、C≡CH、C≡N、可选取代的苯基、呋喃基或噻吩基；A是含有X1的环，X1的含义为O、S、NH、N（CH3）或CH2；X2是O、S或NH；以及式（2）中的化合物，其中R4是可选取代的苯基、可选取代的吡啶基、可选取代的吲哚基、—NR7R8；或—NH—N═CH—R9；且取代基R5到R9的含义在说明书中有所说明，特别是乙硫异烟胺。该药物组合物可用于治疗多药耐药性结核病等疾病。