N-(3-aminophenyl)butyramide hydrochloride salt

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-aminophenyl)butyramide hydrochloride salt
• 英文别名: 3-(((propyl)carbonyl)amino)aniline hydrochloride；N-(3-aminophenyl)butanamide hydrochloride；N-(3-aminophenyl)butanamide;hydrochloride
• 化学式: C₁₀H₁₄N₂O*ClH
• mdl: MFCD12197175
• 分子量: 214.695
• InChiKey: CDYYOANOINUMKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-aminophenyl)butyramide hydrochloride salt 、 2-叠氮苯甲酸 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到2-azido-N-(3-butyramidophenyl)benzamide
  参考文献：
  名称：

  Characterization of Protease-Activated Receptor (PAR) ligands: Parmodulins are reversible allosteric inhibitors of PAR1-driven calcium mobilization in endothelial cells

  摘要：

  Several classes of ligands for Protease-Activated Receptors (PARs) have shown impressive anti-inflammatory and cytoprotective activities, including PAR2 antagonists and the PAR1-targeting parmodulins. In order to support medicinal chemistry studies with hundreds of compounds and to perform detailed mode-of-action studies, it became important to develop a reliable PAR assay that is operational with endothelial cells, which mediate the cytoprotective effects of interest. We report a detailed protocol for an intracellular calcium mobilization assay with adherent endothelial cells in multiwell plates that was used to study a number of known and new PAR1 and PAR2 ligands, including an alkynylated version of the PAR1 antagonist RWJ-58259 that is suitable for the preparation of tagged or conjugate compounds. Using the cell line EA. hy926, it was necessary to perform media exchanges with automated liquid handling equipment in order to obtain optimal and reproducible antagonist concentration-response curves. The assay is also suitable for study of PAR2 ligands; a peptide antagonist reported by Fairlie was synthesized and found to inhibit PAR2 in a manner consistent with reports using epithelial cells. The assay was used to confirm that vorapaxar acts as an irreversible antagonist of PAR1 in endothelium, and parmodulin 2 (ML161) and the related parmodulin RR-90 were found to inhibit PAR1 reversibly, in a manner consistent with negative allosteric modulation. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2018.04.016
• 作为产物：
  描述：

  N-(3-硝基苯基)丁胺 在 palladium 10% on activated carbon 、 氢气 、 盐酸 作用下， 以 甲醇 、 水 、 二氯甲烷 为溶剂， 反应 16.0h， 以92%的产率得到N-(3-aminophenyl)butyramide hydrochloride salt
  参考文献：
  名称：

  Characterization of Protease-Activated Receptor (PAR) ligands: Parmodulins are reversible allosteric inhibitors of PAR1-driven calcium mobilization in endothelial cells

  摘要：

  Several classes of ligands for Protease-Activated Receptors (PARs) have shown impressive anti-inflammatory and cytoprotective activities, including PAR2 antagonists and the PAR1-targeting parmodulins. In order to support medicinal chemistry studies with hundreds of compounds and to perform detailed mode-of-action studies, it became important to develop a reliable PAR assay that is operational with endothelial cells, which mediate the cytoprotective effects of interest. We report a detailed protocol for an intracellular calcium mobilization assay with adherent endothelial cells in multiwell plates that was used to study a number of known and new PAR1 and PAR2 ligands, including an alkynylated version of the PAR1 antagonist RWJ-58259 that is suitable for the preparation of tagged or conjugate compounds. Using the cell line EA. hy926, it was necessary to perform media exchanges with automated liquid handling equipment in order to obtain optimal and reproducible antagonist concentration-response curves. The assay is also suitable for study of PAR2 ligands; a peptide antagonist reported by Fairlie was synthesized and found to inhibit PAR2 in a manner consistent with reports using epithelial cells. The assay was used to confirm that vorapaxar acts as an irreversible antagonist of PAR1 in endothelium, and parmodulin 2 (ML161) and the related parmodulin RR-90 were found to inhibit PAR1 reversibly, in a manner consistent with negative allosteric modulation. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2018.04.016

文献信息

• Guanidine derivatives useful in therapy
  申请人：Astra Aktiebolag

  公开号：US05885985A1

  公开（公告）日：1999-03-23

  Guanidine derivatives of formula I ##STR1## wherein R.sup.8 represents hydrogen, halogen, alkyl C1 to 6, nitro, trifluoromethyl, thioalkyl C1 to 6, hydroxy, alkoxy C1 to 6, or a group selected from --NR.sup.4 R.sup.5, --O(CH.sub.2).sub.p Q, --(CH.sub.2).sub.m OQ, --(CH.sub.2).sub.m NR.sup.1 R.sup.2, --O(CH.sub.2).sub.m NR.sup.1 R.sup.2, --NHCO(CH.sub.2).sub.m NH(CH.sub.2).sub.n Q or --(CH.sub.2).sub.p CONR.sup.1 R.sup.2, or R.sup.8 represents the group A--CO--B; R.sup.9 represents hydrogen, halogen, alkyl C1 to 6, nitro or trifluoromethyl; and R.sup.1, R.sup.2, R.sup.4, R.sup.5, n, m, p, Q, A, B, and W are as defined in the specification, are described together with processes for their manufacture and compositions containing them. Compounds of formula I are useful in therapy.

  公式I的胍基衍生物##STR1##其中R.sup.8代表氢、卤素、烷基C1至6、硝基、三氟甲基、硫代烷基C1至6、羟基、烷氧基C1至6，或者从--NR.sup.4 R.sup.5、--O(CH.sub.2).sub.p Q、--(CH.sub.2).sub.m OQ、--(CH.sub.2).sub.m NR.sup.1 R.sup.2、--O(CH.sub.2).sub.m NR.sup.1 R.sup.2、--NHCO(CH.sub.2).sub.m NH(CH.sub.2).sub.n Q或--(CH.sub.2).sub.p CONR.sup.1 R.sup.2中选择的基团; 或者R.sup.8代表基团A--CO--B; R.sup.9代表氢、卤素、烷基C1至6、硝基或三氟甲基; 而R.sup.1、R.sup.2、R.sup.4、R.sup.5、n、m、p、Q、A、B和W如规范中所定义的，描述了它们的制造过程和含有它们的组合物。公式I的化合物在治疗中是有用的。
• US05998399
  申请人：——

  公开号：——

  公开（公告）日：——
• GUANIDINE DERIVATIVES USEFUL IN THERAPY
  申请人：Astra Aktiebolag

  公开号：EP0690851B1

  公开（公告）日：1999-05-19
• US5885985A
  申请人：——

  公开号：US5885985A

  公开（公告）日：1999-03-23
• US5998399A
  申请人：——

  公开号：US5998399A

  公开（公告）日：1999-12-07