1-(1-苯基环己基)哌啶1-氧化 | 82354-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 1-(1-苯基环己基)哌啶1-氧化
• 英文名称: des-N-methylnoracronycine
• 英文别名: glyfoline；1,6-dihydroxy-2,3,4,5-tetramethoxy-10-methyl-9-acridone；1,6-dihydroxy-2,3,4,5-tetramethoxy-10-methylacridin-9-one
• CAS: 82354-35-6
• 化学式: C₁₈H₁₉NO₇
• 分子量: 361.351
• InChiKey: IHSANOPPEBGTGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  97.7
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(1-苯基环己基)哌啶1-氧化 在 吡啶 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 3.25h， 生成 6-O-[[(4-N-isopropylcarbamoyl)methylpiperazin-1-yl]carbonyl]glyfoline
  参考文献：
  名称：

  Su; Lin; Chen, Medicinal Chemistry Research, 2000, vol. 10, # 3, p. 137 - 148

  摘要：

  DOI：
• 作为产物：
  描述：

  6-(benzyloxy)-1,2,3,4,5-pentamethoxyacridin-9-one 在 palladium on activated charcoal 盐酸 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 1-(1-苯基环己基)哌啶1-氧化
  参考文献：
  名称：

  甘氨酸的合成，甘氨酸是枸杞子的成分（Willd。）Lindl。和潜在的抗癌药

  摘要：

  4-苄氧基-3- methoxyanthranilic酸（缩合3）与5-碘-1,2,3,4-四甲氧基苯（4），得到6-苄氧基1,2,3,4,5-五甲氧基-9-吖啶酮（5），其随后通过N-甲基化，选择性脱-O-甲基化和脱苄基作用转化为乙二醛（1）。合成的草甘膦（1）与从植物中分离出的真实样品完全相同。

  DOI：

  10.1016/s0040-4039(00)74267-5

文献信息

• Synthesis of the acridone alkaloids, glyfoline and congeners. Structure-activity relationship studies of cytotoxic acridones
  作者：Tsann Long Su、Bernd Kohler、Ting Chao Chou、Moon Woo Chun、Kyoichi A. Watanabe

  DOI：10.1021/jm00092a022

  日期：1992.7

  Glyfoline (4, 1,6-dihydroxY-10-methyl-2,3,4,5-tetramethoxyacridin-9-one) and its congeners were synthesized for evaluation of their cytotoxicity. A detailed structure-activity relationships (SAR) of these acridone derivatives were also studied. To study the SAR of glyfoline analogues, substituent(s) at C-1 and C-6 and at the heterocyclic nitrogen of glyfoline nucleus were modified. Nitro- and amino-substituted glyfoline analogues were also synthesized to study the effects of substituent(s) (electron-withdrawing vs electron-donating) on their cytotoxicity. These compounds were synthesized via the Ullmann condensation of anthranilic acids with iodobenzenes or 2-chlorobenzoic acids with aniline-derivatives. The SAR studies showed that 1-hydroxy 9-acridones were more active than their 1-OMe derivatives against cell growth of human leukemic HL-60 cells in culture. Replacement of NMe of glyfoline with NH or N(CH2)2NEt2 resulted in either total loss or dramatic reduction of cytotoxity. Glyfoline congeners with nitro function at the A-ring were inactive, while compounds with amino substituent were shown to be cytotoxic in vitro.
• Wu, Tian-Shung; Furukawa, Hiroshi; Kuoh, Chang-Sheng, Journal of the Chemical Society. Perkin transactions I, 1983, # 8, p. 1681 - 1688
  作者：Wu, Tian-Shung、Furukawa, Hiroshi、Kuoh, Chang-Sheng、Hsu, Kuo-Shih

  DOI：——

  日期：——
• Wu, Tian-Shung; Furukawa, Hiroshi; Kuoh, Chang-Sheng, Heterocycles, 1982, vol. 19, # 6, p. 1047 - 1051
  作者：Wu, Tian-Shung、Furukawa, Hiroshi、Kuoh, Chang-Sheng

  DOI：——

  日期：——
• US5296602A
  申请人：——

  公开号：US5296602A

  公开（公告）日：1994-03-22
• [EN] MULTISUBSTITUTED 1-HYDROXY-9-ACRIDONES WITH ANTICANCER ACTIVITY
  申请人：——

  公开号：WO1992016509A1

  公开（公告）日：1992-10-01

  [FR] Un composé a la structure (I), dans laquelle R2 et R3 sont identiques ou différents et désignent hydrogène, un groupe alkyle saturé ou insaturé ayant 1 à 5 atomes de carbone, un groupe hydroxyle, un groupe alkyloxyle saturé ou insaturé ayant 1 à 5 atomes de carbone, un groupe O-alkyloxyalkyle dans lequel les alkyles sont identiques ou différents et ont 1 à 5 atomes de carbone, un groupe O-aryloxyalkyle dans lequel l'alkyle a 1 à 5 atomes de carbone, un groupe O-acyle, un groupe O-aroyle ou un groupe O-aryle; R4 désigne hydrogène, un groupe alkyle saturé ou insaturé ayant 1 à 5 atomes de carbone, un groupe hydroxyle, un groupe hydroxyméthyle, un groupe alkyloxyle saturé ou insaturé ayant 1 à 5 atomes de carbone, un groupe O-alkyloxyalkyle dans lequel les alkyles sont identiques ou différents et ont 1 à 5 atomes de carbone, un groupe O-aryloxyalkyle dans lequel l'alkyl a 1 à 5 atomes de carbone, un groupe O-alkyloxyalkyloxyalkyle dans lequel les alkyles sont identiques ou différents et ont 1 à 5 atomes de carbone, un groupe O-acyle, un groupe O-aroyle, un groupe O-aryle; R5, R6 et R7 sont identiques ou différents et désignent hydrogène, un groupe alkyle saturé ou insaturé ayant 1 à 5 atomes de carbone, sulfate, phosphate, un groupe hydroxyle, un groupe alkyloxyle saturé ou insaturé ayant 1 à 5 atomes de carbone, un groupe alkyloxyalkyle dans lequel les alkyles sont identiques ou différents et ont 1 à 5 atomes de carbone, un groupe O-aryloxyalkyle dans lequel l'alkyle a 1 à 5 atomes de carbone, un groupe O-acyle, un groupe O-aroyle, un groupe O-aryle, un groupe nitro, un groupe amino, un groupe N-alkylamino ayant 1 à 5 atomes de carbone, un groupe N,N-dialkylamino dans lequel les alkyles ont 1 à 5 atomes de carbone, un groupe aminoalkyloxyle ayant 1 à 5 atomes de carbone, un groupe N-alkyl-aminoalkyloxyle dans lequel les alkyles sont identiques ou différents et ont 1 à 5 atomes de carbone, un groupe N,N-dialkyl-aminoalkyloxyle dans lequel les alkyles sont identiques ou différents et ont 1 à 5 atomes de carbone,un
  [EN] The present invention provides a compound having structure (I) wherein R?2 and R?3 are the same or different and are hydrogen, a saturated or unsaturated alkyl group having 1 to 5 carbon atoms, a hydroxy group, a saturated or unsaturated alkyloxy group having 1 to 5 carbon atoms, an O-alkyloxyalkyl group wherein each alkyl is the same or different having 1 to 5 carbon atoms, an O-aryloxyalkyl group with the alkyl having 1 to 5 carbon atoms, an O-acyl group, an O-aroyl group, or an O-aryl group; R?4 is hydrogen, a saturated or unsaturated alkyl group having 1 to 5 carbon atoms, a hydroxy group, a hydroxymethyl group, a saturated or unsaturated alkyloxy group having 1 to 5 carbon atoms, an O-alkyloxyalkyl group wherein each alkyl is the same or different having 1 to 5 carbon atoms, an O-aryloxyalkyl group with the alkyl having 1 to 5 carbon atoms, an O-alkyloxyalkyloxyalkyl group wherein each alkyl is the same or different having 1 to 5 carbon atoms, an O-acyl group, an O-aroyl group, or an O-aryl group; R?5, R?6, and R?7 are the same or different and are hydrogen, a saturated or unsaturated alkyl group having 1 to 5 carbon atoms, sulfate, phosphate, a hydroxy group, a saturated or unsaturated alkyloxy group having 1 to 5 carbon atoms, an O-alkyloxyalkyl group wherein each alkyl is the same or different having 1 to 5 carbon atoms, an O-aryloxyalkyl group with the alkyl having 1 to 5 carbon atoms, an O-acyl group, an O-aroyl group, an O-aryl group, a nitro group, an amino group, an N-alkylamino group having 1 to 5 carbon atoms, an N,N-dialkylamino group with each alkyl having 1 to 5 carbon atoms, an aminoalkyloxy group having 1 to 5 carbon atoms, an N-alkyl-aminoalkyloxy group wherein each alkyl is the same or different having 1 to 5 carbon atoms, an N,N-dialkyl-aminoalkyloxy group wherein each alkyl is the same or different having 1 to 5 carbon atoms, a quaternary ammonium alkyloxy salt, or a halogen; and R?10 is hydrogen, a saturated or unsaturated alkyl group having 1 to 5 carbon atoms, an aminoalkyl group having 1 to 5 carbon atoms, an N-alkylaminoalkyl group wherein each alkyl is the same or different having 1 to 5 carbon atoms, an N,N-dialkylaminoalkyl group wherein each alkyl is the same or different having 1 to 5 carbon atoms, or an amino acid moiety. The present invention also provides a method for synthesizing a compound having the above-identified structure as well as the intermediate compounds produced according to that method. The present invention further provides a pharmaceutical composition comprising the above compounds. Lastly, the present invention provides a method of inhibiting growth of tumor cells.