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N-(1-(tetrahydro-2H-thiopyran-4-yl)indolin-6-yl)thiophene-2-carboximidamide | 1355181-41-7

中文名称
——
中文别名
——
英文名称
N-(1-(tetrahydro-2H-thiopyran-4-yl)indolin-6-yl)thiophene-2-carboximidamide
英文别名
N'-[1-(thian-4-yl)-2,3-dihydroindol-6-yl]thiophene-2-carboximidamide
N-(1-(tetrahydro-2H-thiopyran-4-yl)indolin-6-yl)thiophene-2-carboximidamide化学式
CAS
1355181-41-7
化学式
C18H21N3S2
mdl
——
分子量
343.517
InChiKey
HZFUGRVPOVKIMY-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):
    4
  • 重原子数:
    23
  • 可旋转键数:
    3
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.39
  • 拓扑面积:
    95.2
  • 氢给体数:
    1
  • 氢受体数:
    4

反应信息

  • 作为反应物:
    描述:
    N-(1-(tetrahydro-2H-thiopyran-4-yl)indolin-6-yl)thiophene-2-carboximidamide盐酸 作用下, 以 甲醇乙醚 为溶剂, 反应 0.17h, 生成 N-(1-(tetrahydro-2H-thiopyran-4-yl)indolin-6-yl)thiophene-2-carboximidamide dihydrochloride
    参考文献:
    名称:
    Discovery of cis-N-(1-(4-(Methylamino)cyclohexyl)indolin-6-yl)thiophene-2-carboximidamide: A 1,6-Disubstituted Indoline Derivative as a Highly Selective Inhibitor of Human Neuronal Nitric Oxide Synthase (nNOS) without Any Cardiovascular Liabilities
    摘要:
    A series of 1,6-disubstituted indoline derivatives were synthesized and evaluated as inhibitors of human nitric oxide synthase (NOS) designed to mitigate the cardiovascular liabilities associated with previously reported tetrahydroquinoline-based selective neuronal NOS inhibitors due to higher lipophilicity (J. Med. Chem. 2011, 54, 5562-5575). This new series produced similar potency and selectivity among the NOS isoforms and was devoid of any cardiovascular liabilities associated with QT prolongation due to hERG activity or endothelial NOS mediated vasoconstriction effect. The SAR studies led to the identification of cis-45, which was shown to reverse thermal hyperalgesia in vivo in the spinal nerve ligation model of neuropathic pain with excellent safety profile (off-target activities at 80 CNS related receptors/ion channels/transporters). The results presented in this report make cis-45 as an ideal tool for evaluating the potential role of selective nNOS inhibitors in CNS related disorders where excess NO produced by nNOS is thought to play a crucial role.
    DOI:
    10.1021/jm201564u
  • 作为产物:
    描述:
    6-nitro-1-(tetrahydro-2H-thiopyran-4-yl)indoline 在 作用下, 以 甲醇乙醇 为溶剂, 反应 18.08h, 生成 N-(1-(tetrahydro-2H-thiopyran-4-yl)indolin-6-yl)thiophene-2-carboximidamide
    参考文献:
    名称:
    Discovery of cis-N-(1-(4-(Methylamino)cyclohexyl)indolin-6-yl)thiophene-2-carboximidamide: A 1,6-Disubstituted Indoline Derivative as a Highly Selective Inhibitor of Human Neuronal Nitric Oxide Synthase (nNOS) without Any Cardiovascular Liabilities
    摘要:
    A series of 1,6-disubstituted indoline derivatives were synthesized and evaluated as inhibitors of human nitric oxide synthase (NOS) designed to mitigate the cardiovascular liabilities associated with previously reported tetrahydroquinoline-based selective neuronal NOS inhibitors due to higher lipophilicity (J. Med. Chem. 2011, 54, 5562-5575). This new series produced similar potency and selectivity among the NOS isoforms and was devoid of any cardiovascular liabilities associated with QT prolongation due to hERG activity or endothelial NOS mediated vasoconstriction effect. The SAR studies led to the identification of cis-45, which was shown to reverse thermal hyperalgesia in vivo in the spinal nerve ligation model of neuropathic pain with excellent safety profile (off-target activities at 80 CNS related receptors/ion channels/transporters). The results presented in this report make cis-45 as an ideal tool for evaluating the potential role of selective nNOS inhibitors in CNS related disorders where excess NO produced by nNOS is thought to play a crucial role.
    DOI:
    10.1021/jm201564u
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文献信息

  • Discovery of <i>cis</i>-<i>N</i>-(1-(4-(Methylamino)cyclohexyl)indolin-6-yl)thiophene-2-carboximidamide: A 1,6-Disubstituted Indoline Derivative as a Highly Selective Inhibitor of Human Neuronal Nitric Oxide Synthase (nNOS) without Any Cardiovascular Liabilities
    作者:Subhash C. Annedi、Jailall Ramnauth、Shawn P. Maddaford、Paul Renton、Suman Rakhit、Gabriela Mladenova、Peter Dove、Sarah Silverman、John S. Andrews、Milena D. Felice、Frank Porreca
    DOI:10.1021/jm201564u
    日期:2012.1.26
    A series of 1,6-disubstituted indoline derivatives were synthesized and evaluated as inhibitors of human nitric oxide synthase (NOS) designed to mitigate the cardiovascular liabilities associated with previously reported tetrahydroquinoline-based selective neuronal NOS inhibitors due to higher lipophilicity (J. Med. Chem. 2011, 54, 5562-5575). This new series produced similar potency and selectivity among the NOS isoforms and was devoid of any cardiovascular liabilities associated with QT prolongation due to hERG activity or endothelial NOS mediated vasoconstriction effect. The SAR studies led to the identification of cis-45, which was shown to reverse thermal hyperalgesia in vivo in the spinal nerve ligation model of neuropathic pain with excellent safety profile (off-target activities at 80 CNS related receptors/ion channels/transporters). The results presented in this report make cis-45 as an ideal tool for evaluating the potential role of selective nNOS inhibitors in CNS related disorders where excess NO produced by nNOS is thought to play a crucial role.
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