4-(苄氧基)-3-甲氧基-2-硝基苯甲酸 | 3584-32-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(苄氧基)-3-甲氧基-2-硝基苯甲酸
• 中文别名: 4-苄氧基-3-甲氧基-2-硝基苯甲酸
• 英文名称: 4-(benzyloxy)-3-methoxy-2-nitrobenzoic acid
• 英文别名: 2-Nitro-3-methoxy-4-benzyloxybenzoesaeure；2-Nitro-vanillinsaeure-benzylaether；4-Benzyloxy-3-methoxy-2-nitro-benzoesaeure；3-methoxy-2-nitro-4-phenylmethoxybenzoic acid
• CAS: 3584-32-5
• 化学式: C₁₅H₁₃NO₆
• 分子量: 303.271
• InChiKey: AWQSWWDWMMXFIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  4-(苄氧基)-3-甲氧基-2-硝基苯甲酸 在 哌啶 、 吡啶 、 copper(I) oxide 、 氯化亚砜 、 sodium dithionite 、 sodium acetate 、 铜 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 三氯氧磷 作用下， 以 二乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 35.0h， 生成 6-(benzyloxy)-10-<2-(diethylamino)ethyl>-1,2,3,4,5-pentamethoxyacridin-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：

  4-羟基-3-甲氧基-2-硝基苯甲醛 在 吡啶 、 sodium hydroxide 、 potassium permanganate 作用下， 生成 4-(苄氧基)-3-甲氧基-2-硝基苯甲酸
  参考文献：
  名称：

  New Compounds-Some Derivatives of Benzylvanillin and Benzylvanillic Acid

  摘要：

  DOI：

  10.1021/ja01179a600

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 glyfoline, a constituent of glycosmis citrifolia (Willd.) Lindl. and a potential anticancer agent
  作者：Tsann-Long Su、Krzysztof Dziewiszek、Tian-Shung Wu

  DOI：10.1016/s0040-4039(00)74267-5

  日期：1991.3

  Condensation of 4-benzyloxy-3-methoxyanthranilic acid (3) with 5-iodo-1,2,3,4-tetramethoxybenzene (4) gave 6-benzyloxy-1,2,3,4,5-pentamethoxy-9-acridone (5), which was then converted into glyfoline (1) via N-methylation, selective de-O-methylation, and debenzylation. The synthetic glyfoline (1) is identical with an authentic sample isolated from plant.

  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。
• The aporphine series. Part I. Developments of the Bischler–Napieralski–Pschorr synthetic method. The synthesis of (±)-isobulbocapnine and (±)-actinodaphnine methyl ether
  作者：D. H. Hey、L. C. Lobo

  DOI：10.1039/jr9540002246

  日期：——
• Synthesis and Biological Evaluation of Novel Analogues of the Pan Class I Phosphatidylinositol 3-Kinase (PI3K) Inhibitor 2-(Difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1<i>H</i>-benzimidazole (ZSTK474)
  作者：Gordon W. Rewcastle、Swarna A. Gamage、Jack U. Flanagan、Raphael Frederick、William A. Denny、Bruce C. Baguley、Philip Kestell、Ripudaman Singh、Jackie D. Kendall、Elaine S. Marshall、Claire L. Lill、Woo-Jeong Lee、Sharada Kolekar、Christina M. Buchanan、Stephen M. F. Jamieson、Peter R. Shepherd

  DOI：10.1021/jm200688y

  日期：2011.10.27

  A structure activity relationship (SAR) study of the pan class I PI 3-kinase inhibitor 2-(difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (ZSTK474) identified substitution at the 4 and 6 positions of the benzimidazole ring as having significant effects on the potency of substituted derivatives. The 6-amino-4-methoxy analogue displayed a greater than 1000-fold potency enhancement over the corresponding 6-aza-4-methoxy analogue against all three class Ia PI 3-kinase enzymes (p110 alpha, p110 beta, and p110 delta) and also displayed significant potency against two mutant forms of the p110 alpha isoform (H1047R and E545K). This compound was also evaluated in vivo against a U87MG human glioblastoma tumor xenograft model in Ragl(-/-) mice, and at a dose of 50 mg/kg given by ip injection at a qd x 10 dosing schedule it dramatically reduced cancer growth by 81% compared to untreated controls.
• US5296602A
  申请人：——

  公开号：US5296602A

  公开（公告）日：1994-03-22

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