methyl 4-<<5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-3-(N-methyl-N-phenylamino)-2-naphthalenyl>carbamoyl>benzoate | 155877-81-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methyl 4-<<5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-3-(N-methyl-N-phenylamino)-2-naphthalenyl>carbamoyl>benzoate
• 英文别名: methyl 4-[[5,5,8,8-tetramethyl-3-(N-methylanilino)-6,7-dihydronaphthalen-2-yl]carbamoyl]benzoate
• CAS: 155877-81-9
• 化学式: C₃₀H₃₄N₂O₃
• 分子量: 470.612
• InChiKey: IMNMEPAQUOKUPO-UHFFFAOYSA-N

物化性质

• 沸点：
  555.5±50.0 °C(predicted)
• 密度：
  1.135±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-<<5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-3-(N-methyl-N-phenylamino)-2-naphthalenyl>carbamoyl>benzoate 在 PPA 作用下， 反应 0.5h， 以66%的产率得到methyl 4-(5,7,7,10,10-pentamethyl-7,8,9,10-tetrahydro-5H-benzo[e]naphtho[2,3-b][1,4]diazepin-13-yl)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
• 作为产物：
  描述：

  (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-3-nitro-2-naphthyl)phenylamine 在 吡啶 、 盐酸 、 铁粉 、 sodium hydride 作用下， 以 乙醇 、 苯 为溶剂， 反应 2.67h， 生成 methyl 4-<<5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-3-(N-methyl-N-phenylamino)-2-naphthalenyl>carbamoyl>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

• 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.