3-苄氧基苯肼盐酸盐 | 109221-90-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-苄氧基苯肼盐酸盐
• 中文别名: 3-苯氧基苯肼盐酸盐
• 英文名称: (3-phenoxyphenyl)hydrazine hydrochloride
• 英文别名: (3-Phenoxyanilino)azanium;chloride；(3-phenoxyanilino)azanium;chloride
• CAS: 109221-90-1
• 化学式: C₁₂H₁₂N₂O*ClH
• 分子量: 236.701
• InChiKey: ASGHYEJXROPEMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.3
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2928000090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  3-苄氧基苯肼盐酸盐 、 氯甲酸丁酯 在 吡啶 作用下， 反应 25.0h， 生成
  参考文献：
  名称：

  恶唑酮选择性抑制胃脂肪分解的恶二唑酮抑制剂减慢脂肪的消化和吸收

  摘要：

  基于先前的研究，并在硅片分子对接实验中，我们设计并合成了一系列新的10 5 -烷氧基Ñ -3-（3- P苯氧基P -苯基）-1,3,4-牛adiazol-2（3H）一衍生物（R m PPOX）。这些分子被进一步评估为哺乳动物消化脂肪酶的选择性和有效抑制剂：纯化的狗胃脂肪酶（DGL）和豚鼠胰腺脂肪酶相关蛋白2（GPLRP2），以及其中所含的猪（PPL）和人（HPL）胰腺脂肪酶猪胰腺提取物（PPE）和人胰液（HPJ）。发现这些化合物能将经典的胰腺脂肪酶（抑制不良）与胃脂肪酶（完全抑制）区分开。其中，5-（2-（Be nzyloxy）ethoxy）-3-（3- P henoxy P henyl ）-1,3,4- Ox adiazol-2（3H）-one（Be m PPOX）被确认为DGL最有效的抑制剂，甚至比FDA批准的药物Orlistat更有活性。来米PPOX和奥利司他进行进一步比较的体外中试

  DOI：

  10.1016/j.ejmech.2016.08.009
• 作为产物：
  描述：

  3-苯氧基苯胺 在 盐酸 、 sodium nitrite 、 tin(ll) chloride 作用下， 以 水 为溶剂， 以81%的产率得到3-苄氧基苯肼盐酸盐
  参考文献：
  名称：

  恶唑酮选择性抑制胃脂肪分解的恶二唑酮抑制剂减慢脂肪的消化和吸收

  摘要：

  基于先前的研究，并在硅片分子对接实验中，我们设计并合成了一系列新的10 5 -烷氧基Ñ -3-（3- P苯氧基P -苯基）-1,3,4-牛adiazol-2（3H）一衍生物（R m PPOX）。这些分子被进一步评估为哺乳动物消化脂肪酶的选择性和有效抑制剂：纯化的狗胃脂肪酶（DGL）和豚鼠胰腺脂肪酶相关蛋白2（GPLRP2），以及其中所含的猪（PPL）和人（HPL）胰腺脂肪酶猪胰腺提取物（PPE）和人胰液（HPJ）。发现这些化合物能将经典的胰腺脂肪酶（抑制不良）与胃脂肪酶（完全抑制）区分开。其中，5-（2-（Be nzyloxy）ethoxy）-3-（3- P henoxy P henyl ）-1,3,4- Ox adiazol-2（3H）-one（Be m PPOX）被确认为DGL最有效的抑制剂，甚至比FDA批准的药物Orlistat更有活性。来米PPOX和奥利司他进行进一步比较的体外中试

  DOI：

  10.1016/j.ejmech.2016.08.009

文献信息

• Synthesis, Opioid Receptor Binding, and Bioassay of Naltrindole Analogues Substituted in the Indolic Benzene Moiety
  作者：Subramaniam Ananthan、Cheryl A. Johnson、Ronald L. Carter、Sarah D. Clayton、Kenner C. Rice、Heng Xu、Peg Davis、Frank Porreca、Richard B. Rothman

  DOI：10.1021/jm980083i

  日期：1998.7.1

  assays in rat or guinea pig brain membranes and for their opioid antagonist and agonist activities in vitro on the guinea pig ileum (GPI) and mouse vas deferens (MVD) preparations. All of the compounds displayed delta selectivity in binding to the delta, mu, and kappa opioid receptors. The binding potencies of most of the compounds at the delta, mu, and kappa sites, however, were lower than that of 1. Among

  δ阿片受体拮抗剂纳曲酮（1）的一系列类似物，在4'-，5'-，6'-或-7'-位置（4-15）和一个通过纳曲酮的Fischer吲哚化反应，在吲哚苯环的5'-位（16）处的2-（2-吡啶基）乙烯基被合成。在大鼠或豚鼠脑膜中的阿片样物质受体结合试验中评估了化合物4-16的亲和力，以及在体外对豚鼠回肠（GPI）和小鼠输精管（MVD）制剂的阿片类拮抗剂和激动剂活性。所有化合物在结合δ，μ和κ阿片受体上均表现出δ选择性。但是，大多数化合物在δ，mu和kappa位的结合力都低于1。通常，7'-取代的化合物比6'-，5'-或4'-取代的类似物具有更高的亲和力，这表明在7'-位置比其他位置对大基团的耐受性更好。为了确定亚型选择剂，还确定了δ和kappa受体的假定亚型的化合物的亲和力：deltacx-1（mu-like），deltacx-2（delta-like）和kappa2b位点。尽管没有发现，但数据显
• Oxadiazolone derivatives, new promising multi-target inhibitors against M. tuberculosis
  作者：Phuong Chi Nguyen、Vincent Delorme、Anaïs Bénarouche、Alexandre Guy、Valérie Landry、Stéphane Audebert、Matthieu Pophillat、Luc Camoin、Céline Crauste、Jean-Marie Galano、Thierry Durand、Priscille Brodin、Stéphane Canaan、Jean-François Cavalier

  DOI：10.1016/j.bioorg.2018.08.025

  日期：2018.12

  A set of 19 oxadiazolone (OX) derivatives have been investigated for their antimycobacterial activity against two pathogenic slow-growing mycobacteria, Mycobacterium marinum and Mycobacterium bovis BCG, and the avirulent Mycobacterium tuberculosis (M. tb) mc(2)6230. The encouraging minimal inhibitory concentrations (MIC) values obtained prompted us to test them against virulent M. tb H37Rv growth either in broth medium or inside macrophages. The OX compounds displayed a diversity of action and were found to act either on extracellular M. tb growth only with moderated MIC50, or both intracellularly on infected macrophages as well as extracellularly on bacterial growth. Of interest, all OX derivatives exhibited very low toxicity towards host macrophages. Among the six potential OXs identified, HPDX, a selective inhibitor of extracellular M. tb growth, was selected and further used in a competitive labelling/enrichment assay against the activity-based probe Desthiobiotin-FP, in order to identify its putative target(s). This approach, combined with mass spectrometry, identified 18 potential candidates, all being serine or cysteine enzymes involved in M. tb lipid metabolism and/or in cell wall biosynthesis. Among them, Ag85A, CaeA, TesA, KasA and MetA have been reported as essential for in vitro growth of M. tb and/or its survival and persistence inside macrophages. Overall, our findings support the assumption that OX derivatives may represent a novel class of multi-target inhibitors leading to the arrest of M. tb growth through a cumulative inhibition of a large number of Ser- and Cys-containing enzymes involved in various important physiological processes.
• Analysis of the discriminative inhibition of mammalian digestive lipases by 3-phenyl substituted 1,3,4-oxadiazol-2(3H)-ones
  作者：Vanessa Point、K.V.P. Pavan Kumar、Sylvain Marc、Vincent Delorme、Goetz Parsiegla、Sawsan Amara、Frédéric Carrière、Gérard Buono、Frédéric Fotiadu、Stéphane Canaan、Julien Leclaire、Jean-François Cavalier

  DOI：10.1016/j.ejmech.2012.10.040

  日期：2012.12

  We report here the reactivity and selectivity of three 5-Methoxy-N-3-Phenyl substituted-1,3,4-Oxadiazol-2(3H)-ones (MPOX, as well as meta and para-PhenoxyPhenyl derivatives, i.e. MmPPOX and MpPPOX) with respect to the inhibition of mammalian digestive lipases: dog gastric lipase (DGL), human (HPL) and porcine (PPL) pancreatic lipases, human (HPLRP2) and guinea pig (GPLRP2) pancreatic lipase-related proteins 2, human pancreatic carboxyl ester hydrolase (hCEH), and porcine pancreatic extracts (PPE). All three oxadiazolones displayed similar inhibitory activities on DGL, PLRP2s and hCEH than the FDA-approved anti-obesity drug Orlistat towards the same enzymes. These compounds appeared however to be discriminative of HPL (poorly inhibited) and PPL (fully inhibited). The inhibitory activities obtained experimentally in vitro were further rationalized using in silico molecular docking. In the case of DGL, we demonstrated that the phenoxy group plays a key role in specific molecular interactions within the lipase's active site. The absence of this group in the case of MPOX, as well as its connectivity to the neighbouring aromatic ring in the case of MmPPOX and MpPPOX, strongly impacts the inhibitory efficiency of these oxadiazolones and leads to a significant gain in selectivity towards the lipases tested. The powerful inhibition of PPL, DGL, PLRP2s, hCEH and to a lesser extend HPL, suggests that oxadiazolone derivatives could also provide useful leads for the development of novel and more discriminative inhibitors of digestive lipases. These inhibitors could be used for a better understanding of individual lipase function as well as for drug development aiming at the regulation of the whole gastrointestinal lipolysis process. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Hahn et al., Croatica Chemica Acta, 1956, vol. 28, p. 57,61
  作者：Hahn et al.

  DOI：——

  日期：——
• [EN] HETEROCYCLIC MODULATORS OF GPR119 FOR TREATMENT OF DISEASE<br/>[FR] MODULATEURS HÉTÉROCYCLIQUES DE GPR119 POUR LE TRAITEMENT D'UNE MALADIE
  申请人：KALYPSYS INC

  公开号：WO2009117421A2

  公开（公告）日：2009-09-24

  The present invention relates to compounds and methods which may be useful as inhibitors of GPR119 for the treatment or prevention of metabolic, cardiovascular, and metabolic diseases.