2,3,4,5-tetramethoxyaniline | 142004-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,3,4,5-tetramethoxyaniline
• CAS: 142004-02-2
• 化学式: C₁₀H₁₅NO₄
• 分子量: 213.233
• InChiKey: DBKBYFROGCHYHE-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100 °C
• 沸点：
  324.8±37.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3,4,5-tetramethoxyaniline 在 palladium on activated charcoal copper(I) oxide 、 盐酸 、 PPA 、 氢气 、 铜 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二乙二醇二甲醚 、 丙酮 为溶剂， 90.0 ℃ 、275.79 kPa 条件下， 反应 35.0h， 生成 7-Amino-1-hydroxy-2,3,4-trimethoxy-10-methyl-10H-acridin-9-one
  参考文献：
  名称：

  Synthesis of the acridone alkaloids, glyfoline and congeners. Structure-activity relationship studies of cytotoxic acridones

  摘要：

  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.

  DOI：

  10.1021/jm00092a022
• 作为产物：
  描述：

  2,3,4-三甲氧基-6-硝基苯甲醛 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 乙醇 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 10.0h， 生成 2,3,4,5-tetramethoxyaniline
  参考文献：
  名称：

  Synthesis of the acridone alkaloids, glyfoline and congeners. Structure-activity relationship studies of cytotoxic acridones

  摘要：

  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.

  DOI：

  10.1021/jm00092a022

文献信息

• Multisubstituted 1-hydroxy-9-acridones with anticancer activity
  申请人：Sloan-Kettering Institute for Cancer Research

  公开号：US05296602A1

  公开（公告）日：1994-03-22

  The present invention provides a compound having the structure: ##STR1## 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.

  本发明提供了一种具有以下结构的化合物：##STR1## 本发明还提供了一种合成具有上述结构的化合物的方法，以及根据该方法产生的中间化合物。本发明还提供了包括上述化合物的药物组合物。最后，本发明提供了一种抑制肿瘤细胞生长的方法。
• Synthesis of Casimiroin and Optimization of Its Quinone Reductase 2 and Aromatase Inhibitory Activities
  作者：Arup Maiti、P. V. Narasimha Reddy、Megan Sturdy、Laura Marler、Scott D. Pegan、Andrew D. Mesecar、John M. Pezzuto、Mark Cushman

  DOI：10.1021/jm801335z

  日期：2009.4.9

  An efficient method has been developed to synthesize casimiroin (1), a component of the edible fruit of Casimiroa edulis, on a multigram scale in good overall yield. The route was versatile enough to provide an array of compound 1 analogues that were evaluated as QR2 and aromatase inhibitors. In addition, X-ray crystallography studies of QR2 in complex with compound 1 and one of its more potent analogues has provided insight into the mechanism of action of this new series of QR2 inhibitors. The initial biological investigations suggest that compound 1 and its analogues merit further investigation as potential chemopreventive or chemotherapeutic agents.
• 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.
• CN116323567
  申请人：——

  公开号：——

  公开（公告）日：——