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(Z)-3-(3,5-di-tert-butyl-2-ethoxyphenyl)but-2-en-1-al | 330934-90-2

中文名称
——
中文别名
——
英文名称
(Z)-3-(3,5-di-tert-butyl-2-ethoxyphenyl)but-2-en-1-al
英文别名
(Z)-3-(3,5-ditert-butyl-2-ethoxyphenyl)but-2-enal
(Z)-3-(3,5-di-tert-butyl-2-ethoxyphenyl)but-2-en-1-al化学式
CAS
330934-90-2
化学式
C20H30O2
mdl
——
分子量
302.457
InChiKey
HQRYVBYLLJOPMX-UVTDQMKNSA-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

物化性质

  • 沸点:
    399.3±31.0 °C(Predicted)
  • 密度:
    0.940±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    6.1
  • 重原子数:
    22
  • 可旋转键数:
    6
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.55
  • 拓扑面积:
    26.3
  • 氢给体数:
    0
  • 氢受体数:
    2

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:
    (Z)-3-(3,5-di-tert-butyl-2-ethoxyphenyl)but-2-en-1-alN,N-二甲基丙烯基脲 、 lithium hydroxide 、 正丁基锂 作用下, 以 四氢呋喃甲醇正己烷 为溶剂, 反应 0.5h, 生成 (2E,4E,6Z)-7-[3,5-bis(1,1-dimethylethyl)-2-ethoxyphenyl]-3-methyl-2,4,6-octatrienoic acid
    参考文献:
    名称:
    Novel (2E,4E,6Z)-7-(2-Alkoxy-3,5-dialkylbenzene)-3-methylocta-2,4,6-trienoic Acid Retinoid X Receptor Modulators Are Active in Models of Type 2 Diabetes
    摘要:
    Previous data have shown that RXR-selective agonists (e.g., 3 and 4) are insulin sensitizers in rodent models of non-insulin-dependent diabetes mellitus (NIDDM). Unfortunately, they also produce dramatic increases in triglycerides and profound suppression of the thyroid hormone axis. Here we describe the design and synthesis of new RXR modulators that retain the insulin-sensitizing activity of RXR agonists but produce substantially reduced side effects. These molecules bind selectively and with high affinity to RXR and, unlike RXR agonists, do not activate RXR homodimers. To further evaluate the antidiabetic activity of these RXR modulators, we have designed a concise and systematic structure-activity relationship around the 2E,4E,6Z-7-aryl-3-methylocta-2,4,6-trienoic acid scaffold. Selected compounds have been evaluated using insulin-resistant rodents (db/db mice) to characterize effects on glucose homeostasis. Our studies demonstrate the effectiveness of RXR modulators in lowering plasma glucose in the db/db mouse model.
    DOI:
    10.1021/jm020340q
  • 作为产物:
    描述:
    (Z)-3-(3,5-di-tert-butyl-2-ethoxyphenyl)but-2-en-1-olN-甲基吲哚酮 、 四丙基高钌酸铵 作用下, 以 二氯甲烷 为溶剂, 以83%的产率得到(Z)-3-(3,5-di-tert-butyl-2-ethoxyphenyl)but-2-en-1-al
    参考文献:
    名称:
    Novel (2E,4E,6Z)-7-(2-Alkoxy-3,5-dialkylbenzene)-3-methylocta-2,4,6-trienoic Acid Retinoid X Receptor Modulators Are Active in Models of Type 2 Diabetes
    摘要:
    Previous data have shown that RXR-selective agonists (e.g., 3 and 4) are insulin sensitizers in rodent models of non-insulin-dependent diabetes mellitus (NIDDM). Unfortunately, they also produce dramatic increases in triglycerides and profound suppression of the thyroid hormone axis. Here we describe the design and synthesis of new RXR modulators that retain the insulin-sensitizing activity of RXR agonists but produce substantially reduced side effects. These molecules bind selectively and with high affinity to RXR and, unlike RXR agonists, do not activate RXR homodimers. To further evaluate the antidiabetic activity of these RXR modulators, we have designed a concise and systematic structure-activity relationship around the 2E,4E,6Z-7-aryl-3-methylocta-2,4,6-trienoic acid scaffold. Selected compounds have been evaluated using insulin-resistant rodents (db/db mice) to characterize effects on glucose homeostasis. Our studies demonstrate the effectiveness of RXR modulators in lowering plasma glucose in the db/db mouse model.
    DOI:
    10.1021/jm020340q
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文献信息

  • Novel (2<i>E</i>,4<i>E</i>,6<i>Z</i>)-7-(2-Alkoxy-3,5-dialkylbenzene)-3-methylocta-2,4,6-trienoic Acid Retinoid X Receptor Modulators Are Active in Models of Type 2 Diabetes
    作者:P. Y. Michellys、R. J. Ardecky、J. H. Chen、D. L. Crombie、G. J. Etgen、A. L. Faulkner、M. M. Faul、T. A. Grese、R. A. Heyman、D. S. Karanewsky、K. Klausing、M. D. Leibowitz、S. Liu、D. A. Mais、C. M. Mapes、K. B. Marschke、A. Reifel-Miller、K. M. Ogilvie、D. Rungta、A. W. Thompson、J. S. Tyhonas、M. F. Boehm
    DOI:10.1021/jm020340q
    日期:2003.6.1
    Previous data have shown that RXR-selective agonists (e.g., 3 and 4) are insulin sensitizers in rodent models of non-insulin-dependent diabetes mellitus (NIDDM). Unfortunately, they also produce dramatic increases in triglycerides and profound suppression of the thyroid hormone axis. Here we describe the design and synthesis of new RXR modulators that retain the insulin-sensitizing activity of RXR agonists but produce substantially reduced side effects. These molecules bind selectively and with high affinity to RXR and, unlike RXR agonists, do not activate RXR homodimers. To further evaluate the antidiabetic activity of these RXR modulators, we have designed a concise and systematic structure-activity relationship around the 2E,4E,6Z-7-aryl-3-methylocta-2,4,6-trienoic acid scaffold. Selected compounds have been evaluated using insulin-resistant rodents (db/db mice) to characterize effects on glucose homeostasis. Our studies demonstrate the effectiveness of RXR modulators in lowering plasma glucose in the db/db mouse model.
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