N-(4-amino-2-benzoylphenyl)phenylacetamide | 265648-22-4

• 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: N-(4-amino-2-benzoylphenyl)phenylacetamide
• 英文别名: N-(4-amino-2-benzoylphenyl)phenylacetic acid amide；N-(4-amino-2-benzoylphenyl)-2-phenylacetamide
• CAS: 265648-22-4
• 化学式: C₂₁H₁₈N₂O₂
• 分子量: 330.386
• InChiKey: KMGKSAHEXHMVTI-UHFFFAOYSA-N

物化性质

• 沸点：
  553.4±50.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-amino-2-benzoylphenyl)phenylacetamide 在 N-甲基吗啉 、 三乙基硅烷 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 生成 N-<3-Benzoyl-4-(2-phenylacetylamino)phenyl>cysteine amide
  参考文献：
  名称：

  Different Amino Acid Replacements in CAAX-Tetrapeptide Based Peptidomimetic Farnesyltransferase Inhibitors

  摘要：

  In a series of CAAX-tetrapeptide based farnesyltransferase inhibitors it has been shown that the central AA-dipeptide can be replaced by tranexamic acid, 4-aminobenzenesulfonic acid, and 3-amino-N-(2,3-dimethylphenyl)benzenesulfonamide, respectively, yielding inhibitors active in the low micromolar range. Lipophilic derivatives of these compounds showed moderate anti-proliferative activity against different tumor cell lines. A promising class of peptidomimetic farnesyltransferase inhibitors was discovered through the replacement of the terminal AAX motif of the CAAX-tetrapeptide by 2-acylamino-5-aminobenzophenones.

  DOI：

  10.1002/(sici)1521-4184(19994)332:4<124::aid-ardp124>3.0.co;2-g
• 作为产物：
  描述：

  2-氨基-5-硝基二苯甲酮 在 tin(ll) chloride 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 6.0h， 生成 N-(4-amino-2-benzoylphenyl)phenylacetamide
  参考文献：
  名称：

  Different Amino Acid Replacements in CAAX-Tetrapeptide Based Peptidomimetic Farnesyltransferase Inhibitors

  摘要：

  In a series of CAAX-tetrapeptide based farnesyltransferase inhibitors it has been shown that the central AA-dipeptide can be replaced by tranexamic acid, 4-aminobenzenesulfonic acid, and 3-amino-N-(2,3-dimethylphenyl)benzenesulfonamide, respectively, yielding inhibitors active in the low micromolar range. Lipophilic derivatives of these compounds showed moderate anti-proliferative activity against different tumor cell lines. A promising class of peptidomimetic farnesyltransferase inhibitors was discovered through the replacement of the terminal AAX motif of the CAAX-tetrapeptide by 2-acylamino-5-aminobenzophenones.

  DOI：

  10.1002/(sici)1521-4184(19994)332:4<124::aid-ardp124>3.0.co;2-g

文献信息

• Non-thiol farnesyltransferase inhibitors: structure–activity relationships of benzophenone-based bisubstrate analogue farnesyltransferase inhibitors
  作者：Martin Schlitzer、Markus Böhm、Isabel Sattler

  DOI：10.1016/s0968-0896(01)00312-1

  日期：2002.3

  structure-activity relationships of benzophenone-based bisubstrate analogue farnesyltransferase inhibitors yielded a bisubstrate analogue farnesyltransferase inhibitor lacking any prenylic or peptidic substructures with nanomolar activity. This represents a considerable progress in comparison to those non-prenylic, non-peptidic bisubstrate analogue farnesyltransferase inhibitors we have described before which

  对基于二苯甲酮的双底物类似物法尼基转移酶抑制剂的结构-活性关系的研究产生了一种双底物类似物法尼基转移酶抑制剂，该抑制剂缺乏任何具有纳摩尔活性的前烯基或肽亚结构。与我们之前所述的那些非烯丙基，非肽双底物类似物法尼基转移酶抑制剂相比，这代表了可观的进步，因为它们利用的AAX拟肽亚结构不同于二苯甲酮，因为这些抑制剂仅在微摩尔范围内显示活性。
• Non-thiol farnesyltransferase inhibitors: n -(4-acylamino-3-benzoylphenyl)-3-[5-(4-nitrophenyl)-2-furyl]acrylic acid amides
  作者：Katja Kettler、Jacek Sakowski、Katrin Silber、Isabel Sattler、Gerhard Klebe、Martin Schlitzer

  DOI：10.1016/s0968-0896(03)00064-6

  日期：2003.4

  have designed the nitrophenylfurylacryl-substituted benzophenone 4f as a non-thiol farnesyltransferase inhibitor utilizing a novel aryl binding site of farnesyltransferase. Variation of the 2-acylamino substituent at the benzophenone core structure of our initial lead 4f yielded several non-thiol farnesyltransferase inhibitors with improved activity. These compounds display activity in the low nanomolar

  我们已经设计了硝基苯呋喃基丙烯酸取代的二苯甲酮4f作为非硫醇法呢基转移酶抑制剂，利用了法呢基转移酶的新型芳基结合位点。我们最初的铅4f的二苯甲酮核心结构处的2-酰基氨基取代基的变化产生了几种具有改进活性的非硫醇法呢基转移酶抑制剂。这些化合物在低纳摩尔范围内显示活性。
• Use of 2-phenylene diamine derivatives for the treatment of infections
  申请人：——

  公开号：US20030036532A1

  公开（公告）日：2003-02-20

  The invention relates to the use of compounds of formula (I), wherein n=0-3; R 1 , R 2 =H, alkyl, aryl, heteroaryl, acyl; R 3 =H, halogen, alkyl, aryl, heteroaryl, arylalkyl, acyl, CN, NO 2 , R 4 —X—; R 4 =H, alkyl, aryl, heteroaryl, aralkyl, acyl; X=NH, O, S, SO 2 , NHSO 2 , OSO 2 , and A, B, C=organic groups. The inventive compounds are used for the prophylaxis and the therapeutic treatment of infectious processes, especially of infectious processes caused by parasites. The invention further relates to medicaments that contain the inventive compounds.

  该发明涉及使用式(I)的化合物，其中n=0-3；R1、R2=H、烷基、芳基、杂环芳基、酰基；R3=H、卤素、烷基、芳基、杂环芳基、芳基烷基、酰基、CN、NO2、R4—X—；R4=H、烷基、芳基、杂环芳基、芳基烷基、酰基；X=NH、O、S、SO2、NHSO2、OSO2，以及A、B、C=有机基团。这些新颖化合物可用于预防和治疗感染过程，特别是由寄生虫引起的感染过程。该发明还涉及含有这些新颖化合物的药物。
• Non-thiol Farnesyltransferase Inhibitors: FTase-Inhibition and Cellular Activity of Benzophenone-based Bisubstrate Analogue Farnesyltransferase Inhibitors
  作者：Andreas Mitsch、Silke Bergemann、Ronald Gust、Isabel Sattler、Martin Schlitzer

  DOI：10.1002/ardp.200300758

  日期：2003.7

  Some 5‐acylaminoacylamino‐benzophenone derivatives were designed as bisubstrate analogue farnesyltransferase inhibitors. These compounds turned out to be only weakly active against farnesyltransferase, but displayed an antiproliferative effect rendering them suitable for further development as a novel type of cytostatic agents.

  一些5-酰基氨基酰基氨基-二苯甲酮衍生物被设计为双底物类似物法呢基转移酶抑制剂。结果表明，这些化合物对法呢基转移酶的活性较弱，但显示出抗增殖作用，使其适合进一步开发为新型细胞抑制剂。
• [DE] AMIDE DES CYSTEINS ALS INHIBITOREN DER FARNESYLTRANSFERASE<br/>[EN] CYSTEINE AMIDES AS FARNESYL TRANSFERASE INHIBITORS<br/>[FR] AMIDES DE LA CYSTEINE COMME INHIBITEURS DE LA FARNESYLTRANSFERASE
  申请人：KNOELL HANS FORSCHUNG EV

  公开号：WO2000027803A1

  公开（公告）日：2000-05-18

  Die Erfindung betrifft Verbindungen der Formel (I) mit inhibitorischen Wirkungen auf die Farnesyltransferase. Einige dieser Verbindungen zeigen eine in vitro Hemmung der Farnesyltransferase bei Konzentrationen < 1 νM. Die erfindungsgemäßen Verbindungen haben die allgemeine Formel (I), worin n = 0 - 3; R1, R2 = H, Alkyl, Aryl, Heteroaryl, Acyl; R3 = H, Halogen, Alkyl, Aryl, Heteroaryl, Arylalkyl, Acyl, CN, NO¿2?, R?4-X-; R4¿ = H, Alkyl, Aryl, Heteroaryl, Aralkyl, Acyl; X = NH, O, S, SO¿2?, NHSO2, OSO2, und A, B, C = organische Reste sind.

  本发明涉及式(I)的连接物，具有对法尼西尔转移酶的抑制作用。其中一些化合物在<1νM的浓度下显示出体外对法尼西尔转移酶的抑制作用。本发明的化合物具有通式(I)，其中n = 0-3; R1，R2 = H，烷基，芳基，杂环芳基，酰基; R3 = H，卤素，烷基，芳基，杂环芳基，芳基烷基，酰基，CN，NO¿2?，R?4-X-; R4¿= H，烷基，芳基，杂环芳基，芳基烷基，酰基; X = NH，O，S，SO¿2?，NHSO2，OSO2，且A，B，C = 有机基。