N-(3-Benzyloxy-pyridin-2-yl)-N'-phenylthiourea

• 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-Benzyloxy-pyridin-2-yl)-N'-phenylthiourea
• 英文别名: N-(3-Benzyloxy-2-pyridyl)-N'-phenylthiourea；1-phenyl-3-(3-phenylmethoxypyridin-2-yl)thiourea
• 化学式: C₁₉H₁₇N₃OS
• 分子量: 335.429
• InChiKey: NGJPMRLICDBXEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-3-苄氧基吡啶 、 硫代异氰酸苯酯 以 甲苯 为溶剂， 以5.6 g (67%)的产率得到N-(3-Benzyloxy-pyridin-2-yl)-N'-phenylthiourea
  参考文献：
  名称：

  [(alkoxy)pyridinyl]amine compounds which are useful in the treatment of

  摘要：

  本发明涉及一般式(I)的N-吡啶基脒和N-吡啶基胍衍生物，其中：Ar.sup.1是可选择取代的苯环；Ar.sup.2是可选择取代的苯环；R.sup.1是氢或C.sub.1-4烷基；R.sup.2是氢或C.sub.1-4烷基；R.sup.3是氢或C.sub.1-4烷基；R.sup.4是氢，卤素，C.sub.1-6烷基或C.sub.1-6烷氧基；X是CH.sub.2或NR.sup.5，R.sup.5是氢或C.sub.1-4烷基，以及它们的盐，以及它们在治疗中作为胃酸分泌抑制剂的用途。

  公开号：

  US05409943A1

文献信息

• [(alkoxy)pyridinyl]amine compounds which are useful in the treatment of
  申请人：SmithKline Beecham Intercredit B.V.

  公开号：US05409943A1

  公开（公告）日：1995-04-25

  The present invention relates to N-pyridylamidine and N-pyridylguanidine derivatives of general formula (I) in which: Ar.sup.1 is an optionally substituted phenyl ring; Ar.sup.2 is an optionally substituted phenyl ring; R.sup.1 is hydrogen or C.sub.1-4 alkyl; R.sup.2 is hydrogen or C.sub.1-4 alkyl; R.sup.3 is hydrogen or C.sub.1-4 alkyl; R.sup.4 is hydrogen, halogen, C.sub.1-6 alkyl or C.sub.1-6 alkoxy; X is CH.sub.2 or NR.sup.5, and R.sup.5 is hydrogen or C.sub.1-4 alkyl, and the salts thereof, and their use in therapy as gastric acid secretion inhibitors.

  本发明涉及一般式(I)的N-吡啶基脒和N-吡啶基胍衍生物，其中：Ar.sup.1是可选择取代的苯环；Ar.sup.2是可选择取代的苯环；R.sup.1是氢或C.sub.1-4烷基；R.sup.2是氢或C.sub.1-4烷基；R.sup.3是氢或C.sub.1-4烷基；R.sup.4是氢，卤素，C.sub.1-6烷基或C.sub.1-6烷氧基；X是CH.sub.2或NR.sup.5，R.sup.5是氢或C.sub.1-4烷基，以及它们的盐，以及它们在治疗中作为胃酸分泌抑制剂的用途。
• PYRIDINE DERIVATIVES, THEIR PREPARATION AND USE AS MEDICINES
  申请人：SMITHKLINE BEECHAM INTERCREDIT B.V.

  公开号：EP0625143A1

  公开（公告）日：1994-11-23
• US5409943A
  申请人：——

  公开号：US5409943A

  公开（公告）日：1995-04-25
• [EN] PYRIDINE DERIVATIVES, THEIR PREPARATION AND USE AS MEDICINES
  申请人：SMITHKLINE BEECHAM INTERCREDIT B.V.

  公开号：WO1993015055A1

  公开（公告）日：1993-08-05

  (EN) The present invention relates to N-pyridylamidine and N-pyridylguanidine derivatives of general formula (I) in which: Ar1 is an optionally substituted phenyl ring; Ar2 is an optionally substituted phenyl ring; R1 is hydrogen or C1-4alkyl; R2 is hydrogen or C1-4alkyl; R3 is hydrogen or C1-4alkyl; R4 is hydrogen, halogen, C1-6alkyl or C1-6alkoxy; X is CH2 or NR5, and R5 is hydrogen or C1-4alkyl, and the salts thereof, and their use in therapy as gastric acid secretion inhibitors.(FR) La présente invention se rapporte à des dérivés de N-pyridylamidine et de N-pyridylguanidine de formule générale (I): dans laquelle Ar1 représente un cycle de phényle éventuellement substitué; Ar2 représente un cycle de phényle éventuellement substitué; R1 représente hydrogène ou alkyle C1-4; R2 représente hydrogène ou alkyle C1-4; R3 représente hydrogène ou alkyle C1-4; R3 représente hydrogène ou alkyle C1-4; R4 représente hydrogène, halogène, alkyle C1-6 ou alkoxy C1-6, X représente CH2 ou NR5, et R5 représente hydrogène ou alkyle C1-4. L'invention concerne également les sels de ces dérivés. Les dérivés sont utiles en thérapie comme inhibiteurs de sécrétion d'acide gastrique.
• Structure-Based Design, Synthesis, and Biological Evaluation of Novel Inhibitors of Human Cyclophilin A
  作者：Jean-François Guichou、Julien Viaud、Clément Mettling、Guy Subra、Yea-Lih Lin、Alain Chavanieu

  DOI：10.1021/jm050716a

  日期：2006.2.1

  Cyclophilin A is involved in many cellular processes, including protein folding and intracellular transports. Because cyclophilin A has been shown to interact with HIV-1 gag proteins and to enhance the viral infectivity, nonimmunosuppressive cyclophilin A ligands may represent a new class of therapeutic agents against HIV. Here, we report a virtual screening using structure- and pharmacophore-based design to identify original nonpeptidic cyclophilin ligands. Following a lead identification of compounds 1 [1-(3-benzyloxypyridin-2-yl)-3-(3-chlorophenyl)urea] and 2 [1-(3-benzyloxypyridin-2-yl)-3-(3-trifluoromethylphenyl)urea] (IC50 = 0.3 mu M), a series of molecules were synthesized from a diarylurea scaffold and evaluated for their in vitro ability to inhibit the cis-trans isomerase activity of cyclophilin A. Molecular modifications provided several more potent compounds, in particular analogues 4d and 4i with IC50 of 14 and 20 nM, respectively. Then, we evaluated the effect of analogues 1 and 2 on HIV virion infectivity in both immortalized and primary cells. Both 1 and 2 reduced virion infectivity in the replication-defective one-round infection assay, but only 1 impaired wild-type HIV infection in human peripheral blood mononuclear cells.