methyl 4-<(3-amino)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido>benzoate | 155877-90-0

• 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: methyl 4-<(3-amino)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido>benzoate
• 英文别名: Methyl 4-[(3-amino-5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2-carbonyl)amino]benzoate
• CAS: 155877-90-0
• 化学式: C₂₃H₂₈N₂O₃
• 分子量: 380.487
• InChiKey: VAOPEZGKGXQDAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-<(3-amino)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido>benzoate 在 吡啶 、 potassium carbonate 、 甲胺 作用下， 以 乙醚 、 乙二醇甲醚 为溶剂， 反应 7.5h， 生成 4-(7,7,10,10-Tetramethyl-2,5-dioxo-1,2,3,5,7,8,9,10-octahydro-naphtho[2,3-e][1,4]diazepin-4-yl)-benzoic acid methyl ester
  参考文献：
  名称：

  Retinobenzoic Acids. 6. Retinoid Antagonists with a Heterocyclic Ring

  摘要：

  Several candidate retinoid antagonists were designed on the basis of the ligand superfamily concept and synthesized. Retinoidal activities of these benzimidazole and benzodiazepine derivatives were examined by assay of differentiation-inducing activity on human promyelocytic leukemia cell line HL-60. The parent benzimidazole derivative, 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnapth[2,3-d]imidazol-2-yl)benzoic acid (7a), and related compounds with a small alkyl group instead of the hydrogen on the nitrogen (N-1) atom of the imidazole ring exhibited retinoidal activity, and the potency strongly depended on the bulkiness of the substituent. The compounds having a phenyl or benzyl group on the nitrogen lacked differentiation-inducing activity on HL-60 cells and acted as antagonists to the potent retinoid 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-napthalenyl)carbamoyl]benzoic acid (Am80). Among the compounds possessing a seven-membered heterocyclic ring as a linking group, 4-(5H-7,8,9,10-tetrahydro-5,7,7,10,10-pentamethylbenzo[e]naphtho[2,3-b][1,4]diazepin-13-yl)benzoic acid (16) also exhibited the antagonistic activity. The binding abilities of these compounds to retinoic acid receptors ct and P were consistent with their potency for the inhibition of HL-60 cell differentiation induced by the retinoid Am80.

  DOI：

  10.1021/jm00036a017
• 作为产物：
  描述：

  5,5,8,8-四甲基-5,6,7,8-四氢-2-萘羧酸 在 吡啶 、 氯化亚砜 、 硫酸 、 硝酸 、 铁粉 、 氯化铵 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 6.5h， 生成 methyl 4-<(3-amino)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido>benzoate
  参考文献：
  名称：

  Retinobenzoic Acids. 6. Retinoid Antagonists with a Heterocyclic Ring

  摘要：

  Several candidate retinoid antagonists were designed on the basis of the ligand superfamily concept and synthesized. Retinoidal activities of these benzimidazole and benzodiazepine derivatives were examined by assay of differentiation-inducing activity on human promyelocytic leukemia cell line HL-60. The parent benzimidazole derivative, 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnapth[2,3-d]imidazol-2-yl)benzoic acid (7a), and related compounds with a small alkyl group instead of the hydrogen on the nitrogen (N-1) atom of the imidazole ring exhibited retinoidal activity, and the potency strongly depended on the bulkiness of the substituent. The compounds having a phenyl or benzyl group on the nitrogen lacked differentiation-inducing activity on HL-60 cells and acted as antagonists to the potent retinoid 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-napthalenyl)carbamoyl]benzoic acid (Am80). Among the compounds possessing a seven-membered heterocyclic ring as a linking group, 4-(5H-7,8,9,10-tetrahydro-5,7,7,10,10-pentamethylbenzo[e]naphtho[2,3-b][1,4]diazepin-13-yl)benzoic acid (16) also exhibited the antagonistic activity. The binding abilities of these compounds to retinoic acid receptors ct and P were consistent with their potency for the inhibition of HL-60 cell differentiation induced by the retinoid Am80.

  DOI：

  10.1021/jm00036a017

文献信息

• Synthesis and Biological Activity of Carboxyphenylquinolines and Related Compounds as New Potent Retinoids. Retinobenzoic Acids. VII.
  作者：Laurence EYROLLES、Emiko KAWACHI、Hiroyuki KAGECHIKA、Yuichi HASHIMOTO、Koichi SHUDO

  DOI：10.1248/cpb.42.2575

  日期：——

  A series of new quinoline, quinolone, and quinazolinedione derivatives was synthesized and tested for retinoid activity in the human promyelocytic cell line HL-60 differentiation assay. All the quinoline compounds exhibited significant activity, depending on the substituent on the heterocycle. However, the quinolone and quinazolinedione derivatives were poor inducers of the differentiation of the HL-60

  合成了一系列新的喹啉，喹诺酮和喹唑啉二酮衍生物，并在人早幼粒细胞系HL-60分化测定中测试了类维生素A的活性。取决于杂环上的取代基，所有喹啉化合物均显示出显着的活性。但是，喹诺酮和喹唑啉二酮衍生物是HL-60细胞分化的弱诱导剂，其活性在很大程度上取决于分子的极性。
• Retinobenzoic Acids. 6. Retinoid Antagonists with a Heterocyclic Ring
  作者：Laurence Eyrolles、Hiroyuki Kagechika、Emiko Kawachi、Hiroshi Fukasawa、Tohru Iijima、Youko Matsushima、Yuichi Hashimoto、Koichi Shudo

  DOI：10.1021/jm00036a017

  日期：1994.5

  Several candidate retinoid antagonists were designed on the basis of the ligand superfamily concept and synthesized. Retinoidal activities of these benzimidazole and benzodiazepine derivatives were examined by assay of differentiation-inducing activity on human promyelocytic leukemia cell line HL-60. The parent benzimidazole derivative, 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnapth[2,3-d]imidazol-2-yl)benzoic acid (7a), and related compounds with a small alkyl group instead of the hydrogen on the nitrogen (N-1) atom of the imidazole ring exhibited retinoidal activity, and the potency strongly depended on the bulkiness of the substituent. The compounds having a phenyl or benzyl group on the nitrogen lacked differentiation-inducing activity on HL-60 cells and acted as antagonists to the potent retinoid 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-napthalenyl)carbamoyl]benzoic acid (Am80). Among the compounds possessing a seven-membered heterocyclic ring as a linking group, 4-(5H-7,8,9,10-tetrahydro-5,7,7,10,10-pentamethylbenzo[e]naphtho[2,3-b][1,4]diazepin-13-yl)benzoic acid (16) also exhibited the antagonistic activity. The binding abilities of these compounds to retinoic acid receptors ct and P were consistent with their potency for the inhibition of HL-60 cell differentiation induced by the retinoid Am80.