4-羟基-N-甲基-3-硝基苯乙酰胺 | 70382-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-羟基-N-甲基-3-硝基苯乙酰胺
• 英文名称: 4-hydroxy-N-methyl-3-nitrobenzeneacetamide
• 英文别名: (4-Hydroxy-3-nitrophenyl)-N-methylacetamid；2-(4-hydroxy-3-nitrophenyl)-N-methylacetamide
• CAS: 70382-04-6
• 化学式: C₉H₁₀N₂O₄
• 分子量: 210.189
• InChiKey: MEHOGVKQEPZGGN-UHFFFAOYSA-N

物化性质

• 熔点：
  127-128.5 °C
• 沸点：
  459.3±35.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-羟基-N-甲基-3-硝基苯乙酰胺 在 platinum(IV) oxide 吡啶 、 氢气 、 potassium carbonate 、 diborane(6) 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 60.0~70.0 ℃ 、344.73 kPa 条件下， 反应 15.25h， 生成 N-<2-methoxy-5-<2-(methylamino)ethyl>phenyl>methanesulfonamide
  参考文献：
  名称：

  N-[2-hydroxy-5-[2-(methylamino)ethyl]phenyl]methanesulfonamide. A potent agonist which releases intracellular calcium by activation of .alpha.1-adrenoceptors

  摘要：

  N-[2-Hydroxy-5-[2-(methylamino)ethyl]phenyl]methanesulfonamide (SK&F 102652) has been prepared and characterized pharmacologically. It is a potent agonist with an EC50 of 25 nM at alpha 1-adrenoceptors as determined in the isolated perfused rabbit ear artery. On the presynaptic alpha 2-adrenoceptors of the guinea pig atrium it was considerably weaker, demonstrating an EC50 for inhibition of neurotransmission of 1200 nM and thus an overall alpha 1/alpha 2 selectivity ratio of greater than or equal to 48. In the vascular smooth muscle of the canine saphenous vein an EC100 concentration of this agonist in the presence of zero external Ca2+ induced 37.9 +/- 1.4% of the maximal contractile response due to this agent while the endogenous ligand norepinephrine evoked only 14.5 +/- 0.4% of the maximum. In the presence of low (1 microM) external calcium, this agent produced 78.3 +/- 5.3% of maximum while norepinephrine gave 45.3 +/- 7.4%. This agent produces alpha 1-adrenoceptor-mediated contraction primarily by release of intracellular Ca2+ and should provide a useful tool for characterizing alpha 1-receptor subtypes.

  DOI：

  10.1021/jm00380a017
• 作为产物：
  描述：

  4-羟基-3-硝基苯乙酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 4-羟基-N-甲基-3-硝基苯乙酰胺
  参考文献：
  名称：

  N-[2-hydroxy-5-[2-(methylamino)ethyl]phenyl]methanesulfonamide. A potent agonist which releases intracellular calcium by activation of .alpha.1-adrenoceptors

  摘要：

  N-[2-Hydroxy-5-[2-(methylamino)ethyl]phenyl]methanesulfonamide (SK&F 102652) has been prepared and characterized pharmacologically. It is a potent agonist with an EC50 of 25 nM at alpha 1-adrenoceptors as determined in the isolated perfused rabbit ear artery. On the presynaptic alpha 2-adrenoceptors of the guinea pig atrium it was considerably weaker, demonstrating an EC50 for inhibition of neurotransmission of 1200 nM and thus an overall alpha 1/alpha 2 selectivity ratio of greater than or equal to 48. In the vascular smooth muscle of the canine saphenous vein an EC100 concentration of this agonist in the presence of zero external Ca2+ induced 37.9 +/- 1.4% of the maximal contractile response due to this agent while the endogenous ligand norepinephrine evoked only 14.5 +/- 0.4% of the maximum. In the presence of low (1 microM) external calcium, this agent produced 78.3 +/- 5.3% of maximum while norepinephrine gave 45.3 +/- 7.4%. This agent produces alpha 1-adrenoceptor-mediated contraction primarily by release of intracellular Ca2+ and should provide a useful tool for characterizing alpha 1-receptor subtypes.

  DOI：

  10.1021/jm00380a017

文献信息

• Use of .alpha..sub.1A -selective adrenoceptor agonists for the treatment
  申请人：Synaptic Pharmaceutical Corporation

  公开号：US05610174A1

  公开（公告）日：1997-03-11

  The present invention provides a method of treating urinary incontinence in a subject which comprises administering to the subject a therapeutically effective amount of a compound having the following structure: ##STR1## wherein each of the substiutents for the compound is as defined in the specification.

  本发明提供了一种治疗患者尿失禁的方法，包括向患者施用具有以下结构的化合物的治疗有效量：##STR1## 其中化合物的每个取代基如规范中所定义。
• DEMARINIS, R. M.;LAVANCHY, P.;HIEBLE, J. P.;JIM, K. F.;MATTHEWS, W. D., J. MED. CHEM., 1985, 28, N 2, 245-248
  作者：DEMARINIS, R. M.、LAVANCHY, P.、HIEBLE, J. P.、JIM, K. F.、MATTHEWS, W. D.

  DOI：——

  日期：——
• THE USE OF ALPHA-1C-SELECTIVE ADRENOCEPTOR AGONISTS FOR THE TREATMENT OF URINARY INCONTINENCE
  申请人：SYNAPTIC PHARMACEUTICAL CORPORATION

  公开号：EP0835107A1

  公开（公告）日：1998-04-15
• US5610174A
  申请人：——

  公开号：US5610174A

  公开（公告）日：1997-03-11
• [EN] THE USE OF ALPHA-1C-SELECTIVE ADRENOCEPTOR AGONISTS FOR THE TREATMENT OF URINARY INCONTINENCE<br/>[FR] UTILISATION D'AGENTS AGONISTES DU RECEPTEUR ADRENERGIQUE ALPHA-1C-SELECTIF DANS LE TRAITEMENT DE L'INCONTINENCE URINAIRE
  申请人：SYNAPTIC PHARMACEUTICAL CORPORATION

  公开号：WO1996038143A1

  公开（公告）日：1996-12-05

  (EN) The present invention provides a method of treating urinary incontinence in a subject which comprises administering to the subject a therapeutically effective amount of an $g(a)1C selective agonist which activates a human $g(a)1C adrenoceptor at least ten-fold more than it activates a human $g(a)1A adrenoceptor and a human $g(a)1B adrenoceptor. The present invention further provides a method of inducing contraction of urethra and bladder neck tissues which comprises contacting the urethra and bladder neck tissues with an effective contraction-inducing amount of an $g(a)1C selective agonist which activates a human $g(a)1C adrenoceptor at least ten-fold more than it activates a human $g(a)1A adrenoceptor and a human $g(a)1B adrenoceptor. In addition, the invention includes compounds for the treatment of urinary incontinence and for use in inducing contraction of urethra and bladder neck tissues.(FR) Cette invention se rapporte à un procédé pour traiter l'incontinence urinaire chez un sujet, procédé qui consiste à administrer à ce sujet une quantité thérapeutiquement efficace d'un agent agoniste $g(a)1C sélectif qui active un récepteur $g(a)1C-adrénergique humain au moins dix fois plus qu'il n'active un récepteur $g(a)1A adrénergique humain et un récepteur $g(a)1B adrénergique humain. Cette invention se rapporte en outre à un procédé pour provoquer une contraction de tissus de l'urètre et du col vesical, ce procédé consistant à mettre en contact ces tissus de l'urètre et du col vesical avec une quantité d'un agent agoniste $g(a)1C-sélectif propre à produire une contraction, cet agent agoniste activant à un récepteur $g(a)1C-adrénergique humain au moins dix fois plus qu'il n'active un récepteur $g(a)1A adrénergique humain et un récepteur $g(a)1B adrénergique humain. Cette invention se rapporte également à des composés pour traiter l'incontinence urinaire et pour servir à provoquer une contraction des tissus de l'urètre et du col vesical.