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2-n-butyl-1,3-bis(4-methoxyphenyl)propane-1,3-dione | 322399-91-7

中文名称
——
中文别名
——
英文名称
2-n-butyl-1,3-bis(4-methoxyphenyl)propane-1,3-dione
英文别名
2-Butyl-1,3-bis(4-methoxyphenyl)propane-1,3-dione
2-n-butyl-1,3-bis(4-methoxyphenyl)propane-1,3-dione化学式
CAS
322399-91-7
化学式
C21H24O4
mdl
——
分子量
340.419
InChiKey
SREUTJGNMABCSO-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    5.1
  • 重原子数:
    25
  • 可旋转键数:
    9
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.33
  • 拓扑面积:
    52.6
  • 氢给体数:
    0
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    2-n-butyl-1,3-bis(4-methoxyphenyl)propane-1,3-dione三溴化硼 作用下, 以 四氢呋喃二氯甲烷N,N-二甲基甲酰胺 为溶剂, 生成 4-[4-Butyl-5-(4-hydroxyphenyl)-2-phenylpyrazol-3-yl]phenol
    参考文献:
    名称:
    Pyrazole Ligands:  Structure−Affinity/Activity Relationships and Estrogen Receptor-α-Selective Agonists
    摘要:
    We have found that certain tetrasubstituted pyrazoles are high-affinity ligands for the estrogen receptor (ER) (Fink et al. Chem. Biol. 1999, 6, 205-219) and that one pyrazole is considerably more potent as an agonist on the ER alpha than on the ER beta subtype (Sun et al. Endocrinology 1999, 140, 800-804). To investigate what substituent pattern provides optimal ER binding affinity and the greatest enhancement of potency as an ER alpha -selective agonist, we prepared a number of tetrasubstituted pyrazole analogues with defined variations at certain substituent positions. Analysis of their binding affinity pattern shows that a C(4)-propyl substituent is optimal and that a p-hydroxyl group on the N(1)-phenyl group also enhances affinity and selectivity for ER alpha. The best compound in this series, a propylpyrazole triol (PPT, compound 4g), binds to ER alpha with high affinity (ca. 50% that of estradiol), and it has a 410-fold binding affinity preference for ER alpha. It also activates gene transcription only through ER alpha. Thus, this compound represents the first ER alpha -specific agonist. We investigated the molecular basis for the exceptional ER alpha binding affinity and potency selectivity of pyrazole 4g by a further study of structure-affinity relationships in this series and by molecular modeling. These investigations suggest that the pyrazole triols prefer to bind to ER alpha with their C(3)-phenol in the estradiol A-ring binding pocket and that binding selectivity results from differences in the interaction of the pyrazole core and C(4)-propyl group with portions of the receptor where ER alpha has a smaller residue than ER beta. These ER subtype-specific interactions and the ER subtype-selective ligands that can be derived from them should prove useful in defining those biological activities in estrogen target cells that can be selectively activated through ER alpha.
    DOI:
    10.1021/jm000170m
  • 作为产物:
    描述:
    己酸 在 PPA 、 lithium hexamethyldisilazane 作用下, 以 四氢呋喃 为溶剂, 反应 3.0h, 生成 2-n-butyl-1,3-bis(4-methoxyphenyl)propane-1,3-dione
    参考文献:
    名称:
    Pyrazole Ligands:  Structure−Affinity/Activity Relationships and Estrogen Receptor-α-Selective Agonists
    摘要:
    We have found that certain tetrasubstituted pyrazoles are high-affinity ligands for the estrogen receptor (ER) (Fink et al. Chem. Biol. 1999, 6, 205-219) and that one pyrazole is considerably more potent as an agonist on the ER alpha than on the ER beta subtype (Sun et al. Endocrinology 1999, 140, 800-804). To investigate what substituent pattern provides optimal ER binding affinity and the greatest enhancement of potency as an ER alpha -selective agonist, we prepared a number of tetrasubstituted pyrazole analogues with defined variations at certain substituent positions. Analysis of their binding affinity pattern shows that a C(4)-propyl substituent is optimal and that a p-hydroxyl group on the N(1)-phenyl group also enhances affinity and selectivity for ER alpha. The best compound in this series, a propylpyrazole triol (PPT, compound 4g), binds to ER alpha with high affinity (ca. 50% that of estradiol), and it has a 410-fold binding affinity preference for ER alpha. It also activates gene transcription only through ER alpha. Thus, this compound represents the first ER alpha -specific agonist. We investigated the molecular basis for the exceptional ER alpha binding affinity and potency selectivity of pyrazole 4g by a further study of structure-affinity relationships in this series and by molecular modeling. These investigations suggest that the pyrazole triols prefer to bind to ER alpha with their C(3)-phenol in the estradiol A-ring binding pocket and that binding selectivity results from differences in the interaction of the pyrazole core and C(4)-propyl group with portions of the receptor where ER alpha has a smaller residue than ER beta. These ER subtype-specific interactions and the ER subtype-selective ligands that can be derived from them should prove useful in defining those biological activities in estrogen target cells that can be selectively activated through ER alpha.
    DOI:
    10.1021/jm000170m
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同类化合物

(2Z)-1,3-二苯基-2-丙烯-1-酮,2-丙烯-1-酮,1,3-二苯基-,(2Z)- 龙血素D 龙血素A 龙血素 B 黄色当归醇F 黄色当归醇B 黄腐醇; 黄腐酚 黄腐醇 D; 黄腐酚 D 黄腐酚B 黄腐酚 黄腐酚 黄卡瓦胡椒素 C 高紫柳查尔酮 阿普非农 阿司巴汀 阿伏苯宗 金鸡菊查耳酮 邻肉桂酰苯甲酸 达泊西汀杂质25 豆蔻明 补骨脂色烯查耳酮 补骨脂查耳酮 补骨脂呋喃查耳酮 补骨脂乙素 蜡菊亭; 4,2',4'-三羟基-6'-甲氧基查耳酮 苯酚,4-[3-(2-羟基苯基)-1-苯基丙基]-2-(3-苯基丙基)- 苯磺酰胺,N-[4-[3-(3-羟基苯基)-1-羰基-2-丙烯基]苯基]- 苯磺酰胺,N-[3-[3-(4-羟基-3-甲氧苯基)-1-羰基-2-丙烯基]苯基]- 苯磺酰胺,4-甲氧基-N,N-二甲基-2-(3-羰基-3-苯基-1-丙烯基)-,(E)- 苯磺酰氯化,4,5-二甲氧基-2-(3-羰基-3-苯基-1-丙烯基)-,(E)- 苯磺酰氯,4-甲氧基-3-(3-羰基-3-苯基-1-丙烯基)-,(E)- 苯甲醇,4-甲氧基-a-[2-(4-甲氧苯基)乙烯基]- 苯甲酸-[4-(3-氧代-3-苯基-丙烯基)-苯胺] 苯甲酸,3-[3-(4-溴苯基)-1-羰基-2-丙烯基]-4-羟基- 苯甲酰(2-羟基苯酰)甲烷 苯甲腈,4-(1-羟基-3-羰基-3-苯基丙基)- 苯基[2-(1-萘基)乙烯基]甲酮 苯基-(三苯基-丙-2-炔基)-醚 苯基-(2-苯基-2,3-二氢-苯并噻唑-2-基)-甲酮 苯亚甲基苯乙酮 苯乙酰腈,a-(1-氨基-2-苯基亚乙基)- 苯丙酸,a-苯甲酰-b-羰基-,苯基(苯基亚甲基)酰肼 苯,1-(2,2-二甲基-3-苯基丙基)-2-甲基- 苏木查耳酮 苄桂哌酯 苄基(4-氯-2-(3-氧代-1,3-二苯基丙基)苯基)氨基甲酸酯 芦荟提取物 腈苯唑 胀果甘草宁C 聚磷酸根皮酚