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2-(dimethylamino)ethyl 4-(octylamino)benzoate | 1012103-31-9

中文名称
——
中文别名
——
英文名称
2-(dimethylamino)ethyl 4-(octylamino)benzoate
英文别名
——
2-(dimethylamino)ethyl 4-(octylamino)benzoate化学式
CAS
1012103-31-9
化学式
C19H32N2O2
mdl
——
分子量
320.475
InChiKey
HTIAPVXKEFVTOQ-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):
    5.8
  • 重原子数:
    23
  • 可旋转键数:
    13
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.63
  • 拓扑面积:
    41.6
  • 氢给体数:
    1
  • 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
  • 下游产品
    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-(dimethylamino)ethyl 4-(octylamino)benzoateN-氯代丁二酰亚胺 作用下, 以 乙腈 为溶剂, 以71%的产率得到2-(dimethylamino)ethyl 4-(octylamino)-3-chlorobenzoate
    参考文献:
    名称:
    丁卡因支架芳香部分的卤素取代基提高了环核苷酸门控通道阻滞的效力
    摘要:
    制备了一系列在芳环上带有取代基的新丁卡因衍生物,并评估了其对视网膜杆状环核苷酸门控 (CNG) 通道的阻断作用。从碱性丁卡因支架开始,芳香取代几乎没有影响,但吸电子取代基显着提高了丁卡因的辛基尾衍生物的阻断效力。特别是,环上 2 位或 3 位的卤素取代导致化合物的效力比母体辛基尾衍生物强 8 倍,比丁卡因强 50 倍。
    DOI:
    10.1016/j.bmcl.2011.08.092
  • 作为产物:
    参考文献:
    名称:
    Cyclic Nucleotide-Gated Channel Block by Hydrolysis-Resistant Tetracaine Derivatives
    摘要:
    To meet a pressing need for better cyclic nucleotide-gated (CNG) channel antagonists, we have increased the biological stability of tetracaine-based blockers by synthesizing amide and thioamide linkage substitutions of tetracaine (1) and a higher affinity octyl tail derivative (5). We report the apparent K-D values, the mechanism of block, and the in vitro hydrolysis rates for these compounds. The ester linkage substitutions did not adversely affect CNG channel block; unexpectedly, thioamide substitution in 1 (compound 8) improved block significantly. Furthermore, the ester linkage substitutions did not appear to affect the mechanism of block in terms of the strong state preference for closed channels. All ester substituted compounds, especially the thioamide substitutions, were more resistant to hydrolysis by serum cholinesterase than their ester counterparts. These findings have implications for dissecting the physiological roles of CNG channels, treating certain forms of retinal degeneration, and possibly the current clinical uses of compound 1.
    DOI:
    10.1021/jm200495g
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文献信息

  • DERIVATIVES OF TETRACAINE
    申请人:WILLAMETTE UNIVERSITY
    公开号:US20140018422A1
    公开(公告)日:2014-01-16
    Disclosed herein are derivatives of tetracaine that, among other things, block cyclic nucleotide gated (CNG) channels and are useful in the treatment of diseases characterized by overactive CNG channels such as retinal degeneration diseases.
    本发明公开了丁卡因衍生物,其除了其他作用外,还能阻断环核苷酸门控(CNG)通道,并可用于治疗由过度活跃的CNG通道引起的疾病,如视网膜退行性疾病。
  • Block of cyclic nucleotide-gated channels by tetracaine derivatives: Role of apolar interactions at two distinct locations
    作者:Timothy Strassmaier、Sarah R. Kirk、Tapasree Banerji、Jeffrey W. Karpen
    DOI:10.1016/j.bmcl.2007.11.069
    日期:2008.1
    A series of new tetracaine derivatives was synthesized to explore the effects of hydrophobic character on blockade of cyclic nucleotide-gated (CNG) channels. Increasing the hydrophobicity at either of two positions on the tetracaine scaffold, the tertiary amine or the butyl tail, yields blockers with increased potency. However, shape also plays an important role. While gradual increases in length of the butyl tail lead to increased potency, substitution of the butyl tail with branched alkyl or cyclic groups is deleterious. (c) 2007 Elsevier Ltd. All rights reserved.
  • US9458102B2
    申请人:——
    公开号:US9458102B2
    公开(公告)日:2016-10-04
  • Cyclic Nucleotide-Gated Channel Block by Hydrolysis-Resistant Tetracaine Derivatives
    作者:Adriana L. Andrade、Kenneth Melich、G. Gregory Whatley、Sarah R. Kirk、Jeffrey W. Karpen
    DOI:10.1021/jm200495g
    日期:2011.7.14
    To meet a pressing need for better cyclic nucleotide-gated (CNG) channel antagonists, we have increased the biological stability of tetracaine-based blockers by synthesizing amide and thioamide linkage substitutions of tetracaine (1) and a higher affinity octyl tail derivative (5). We report the apparent K-D values, the mechanism of block, and the in vitro hydrolysis rates for these compounds. The ester linkage substitutions did not adversely affect CNG channel block; unexpectedly, thioamide substitution in 1 (compound 8) improved block significantly. Furthermore, the ester linkage substitutions did not appear to affect the mechanism of block in terms of the strong state preference for closed channels. All ester substituted compounds, especially the thioamide substitutions, were more resistant to hydrolysis by serum cholinesterase than their ester counterparts. These findings have implications for dissecting the physiological roles of CNG channels, treating certain forms of retinal degeneration, and possibly the current clinical uses of compound 1.
  • Halogen substituents on the aromatic moiety of the tetracaine scaffold improve potency of cyclic nucleotide-gated channel block
    作者:Sarah R. Kirk、Adriana L. Andrade、Kenneth Melich、Evan P. Jackson、Elysia Cuellar、Jeffrey W. Karpen
    DOI:10.1016/j.bmcl.2011.08.092
    日期:2011.11
    tetracaine derivatives with substituents on the aromatic ring was prepared and evaluated for block of retinal rod cyclic nucleotide-gated (CNG) channels. Aromatic substitutions had little effect starting with the basic tetracaine scaffold, but electron-withdrawing substituents significantly improved the blocking potency of an octyl-tail derivative of tetracaine. In particular, halogen substitutions at either
    制备了一系列在芳环上带有取代基的新丁卡因衍生物,并评估了其对视网膜杆状环核苷酸门控 (CNG) 通道的阻断作用。从碱性丁卡因支架开始,芳香取代几乎没有影响,但吸电子取代基显着提高了丁卡因的辛基尾衍生物的阻断效力。特别是,环上 2 位或 3 位的卤素取代导致化合物的效力比母体辛基尾衍生物强 8 倍,比丁卡因强 50 倍。
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