4-(4-氯-苯基)-5-甲基-2H-3-氨基吡唑 | 214416-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(4-氯-苯基)-5-甲基-2H-3-氨基吡唑
• 英文名称: 4-(4-chlorophenyl)-5-methyl-1H-pyrazol-3-amine
• 英文别名: 4-(4-chlorophenyl)-3-methyl-1H-pyrazol-5-amine
• CAS: 214416-39-4
• 化学式: C₁₀H₁₀ClN₃
• mdl: MFCD00737209
• 分子量: 207.662
• InChiKey: PIYGPVNFVWLQAG-UHFFFAOYSA-N

物化性质

• 溶解度：
  14 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  4-(4-氯-苯基)-5-甲基-2H-3-氨基吡唑 在 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 生成 7-Chloro-3-(4-chlorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  The discovery of 4-(3-pentylamino)-2,7-dimethyl-8-(2-methyl-4-methoxyphenyl)-pyrazolo-[1,5- a ]-pyrimidine: A corticotropin-releasing factor (hCRF 1 ) antagonist

  摘要：

  Structure-activity relationship studies led to the discovery of 4-(3-pentylamino)-2,7-dimethyl-8-(2-methyl-4-methoxyphenyl)-pyrazolo-[1,5-a]-pyrimidine 11-31 (DMP904), whose pharmacological profile strongly supports the hypothesis that hCRF(1) antagonists may be potent anxiolytic drugs. Compound 11-31 (hCRF(1) K-i= 1.0 +/- 0.2 nM (n = 8)) was a potent antagonist of hCRF(1)-coupled adenylate cyclase activity in HEK293 cells (IC50 = 10.0 +/- 0.01 nM versus 10 nM r/hCRF, I? = 8); alpha-helical CRF(9-41) had weaker potency (IC50 = 286 +/- 63 nM, n = 3). Analogue 11-31 had good oral activity in the rat situational anxiety test; the minimum effective dose for 11-31 was 0.3 mg/kg (po). Maximal efficacy (approximately 57% reduction in latency lime in the dark compartment) was observed at this dose. Chlordiazepoxide caused a 72% reduction in latency at 20 mg/kg (po). The literature compound 1 (CP154526-1. 30 mg/kg (po)) was inactive in this lest. Compound 11-31 did not inhibit open-field locomotor activity at 10, 30, and 100 mg/kg (po) in rats. In beagle dogs, this compound (5 mg/kg, iv, po) afforded good plasma levels. The key iv pharmacokinetic parameters were t(1/2), CL and V-d.ss values equal to 46.4 +/- 7.6 h, 0.49 +/- 0.08 L/kg/h and 23.0 +/- 4.2 L/kg, respectively. After oral dosing. the mean C-max, T-max, t(1/2) and bioavailability values were equal to 1260 +/- 290 nM, 0.75 +/- 0.25 h, 45.1 +/- 10.2 h and 33.1%, respectively. The overall rat behavioral profile of this compound suggests that it may be an anxiolytic drug with a low motor side effect Liability. (C) 2000 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00271-0
• 作为产物：
  描述：

  对氯苯乙腈 在 盐酸肼 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 mineral oil 为溶剂， 反应 0.08h， 生成 4-(4-氯-苯基)-5-甲基-2H-3-氨基吡唑
  参考文献：
  名称：

  N-Acetyl-3-aminopyrazoles block the non-canonical NF-kB cascade by selectively inhibiting NIK

  摘要：

  由于击中导向优化，氨基吡唑3a是一种选择性超过44种激酶的NIK抑制剂。

  DOI：

  10.1039/c8md00068a

文献信息

• HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
  申请人：McCall John M.

  公开号：US20120277224A1

  公开（公告）日：2012-11-01

  Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

  本文披露了新的杂环化合物和组合物，以及它们作为药物治疗疾病的应用。还提供了抑制PAS激酶（PASK）在人类或动物主体中活性的方法，用于治疗疾病，如糖尿病。
• NOVEL COMPOUND ACTING AS A CANNABINOID RECEPTOR-1 INHIBITOR
  申请人：Shin Song Seok

  公开号：US20130158025A1

  公开（公告）日：2013-06-20

  Disclosed is a novel compound acting as a cannabinoid receptor 1 inhibitor, a prodrug thereof, an isomer thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof. The novel compound or the like is useful for preventing or treating diseases mediated by the cannabinoid receptor-1.

  公开的是一种作为大麻素受体1抑制剂的新化合物，其前体，异构体，其药用可接受盐，水合物或溶剂化合物。该新化合物或类似物对预防或治疗由大麻素受体1介导的疾病有用。
• Three-component condensations with 5-amino-4-phenylpyrazole
  作者：D. V. Kryl’skii、Kh. S. Shikhaliev、A. S. Chuvashlev

  DOI：10.1134/s107042801003019x

  日期：2010.3

  3-methyl(or methoxymethyl)-4-phenyl-1H-pyrazol-5-amine with triethyl orthoformate and carbonyl compounds or nitriles containing an activated methylene group (cyclohexane-1,3-diones, acetoacetanilides, benzoylacetone, ethyl cyanoacetate, malononitrile, 1H-benzimidazol-2-ylacetonitrile) gave substituted pyrazolopyrimidines and pyrazoloquinazolines.

  3-甲基（或甲氧基甲基）-4-苯基-1 H-吡唑-5-胺与原甲酸三乙酯和含有活化亚甲基的羰基化合物或腈的三组分缩合反应（环己烷-1,3-二酮，乙酰乙酰苯胺，苯甲酰丙酮氰基乙酸乙酯，丙二腈，1 H-苯并咪唑-2-基乙腈）得到取代的吡唑并嘧啶和吡唑并喹唑啉。
• Structure–Activity Relationships of Pyrazolo[1,5-<i>a</i>]pyrimidin-7(4<i>H</i>)-ones as Antitubercular Agents
  作者：Sangmi Oh、M. Daben J. Libardo、Shaik Azeeza、Gary T. Pauly、Jose Santinni O. Roma、Andaleeb Sajid、Yoshitaka Tateishi、Caroline Duncombe、Michael Goodwin、Thomas R. Ioerger、Paul G. Wyatt、Peter C. Ray、David W. Gray、Helena I. M. Boshoff、Clifton E. Barry

  DOI：10.1021/acsinfecdis.0c00851

  日期：2021.2.12

  various modes of action against Mycobacterium tuberculosis (Mtb). We explored this scaffold through the synthesis of a focused library of analogues and identified key features of the pharmacophore while achieving substantial improvements in antitubercular activity. Our best hits had low cytotoxicity and showed promising activity against Mtb within macrophages. The mechanism of action of these compounds

  Pyrazolo[1,5 - a ]pyrimidin-7(4 H )-one 通过高通量全细胞筛选被鉴定为潜在的抗结核药物。该支架的核心之前已被多次鉴定，并且与抗结核分枝杆菌( Mtb ) 的各种作用模式有关。我们通过合成一个集中的类似物库探索了这种支架，并确定了药效团的关键特征，同时实现了抗结核活性的显着改善。我们的最佳产品具有低细胞毒性，并显示出对Mtb的有希望的活性巨噬细胞内。这些化合物的作用机制与细胞壁生物合成、异戊二烯生物合成或铁吸收无关，正如其他具有这种核心结构的化合物所发现的那样。黄素腺嘌呤二核苷酸 (FAD) 依赖性羟化酶 (Rv1751) 的突变赋予了对这些化合物的抗性，该羟化酶通过分子氧的羟基化促进化合物分解代谢。我们的结果强调了化学聚集的风险，但没有建立化学相关生长抑制剂的机制相似性。
• Highly regioselective synthesis of trifluoromethyl derivatives of pyrazolo[1,5-a]pyrimidines bearing fused cycloalkane rings using (2-ethoxycycloalkenyl)-2,2,2-trifluoroethanones
  作者：Elena E. Emelina、Aleksander A. Petrov、Stanislav I. Selivanov、Yulia V. Nelyubina、Mikhail Yu. Antipin

  DOI：10.1016/j.jfluchem.2009.06.014

  日期：2009.10

  8-Trifluoromethyl-6,7-dihydro-5H-1,4,8a-triaza-s-indacene and 9-trifluoromethyl-5,6,7,8-tetrahydropyrazolo[5,1-b]quinazolines were efficiently generated by condensation of 5(3)-aminopyrazoles with (2-ethoxycycloalkenyl)-2,2,2-trifluoroethanones and isolated in excellent yields. The regiochemistry of the prepared compounds was established by 1H, 13C and 19F NMR spectroscopy and X-ray diffraction analysis

  -8-三氟甲基-6,7-二氢-5- ħ -1,4,8a三氮杂-小号-indacene和9-三氟甲基-5,6,7,8-四氢[5,1- b被有效地生成]喹唑啉5（3）-氨基吡唑类与（2-乙氧基环烯基）-2,2,2-三氟乙炔的缩合反应，收率高。通过1 H，13 C和19 F NMR光谱法和X射线衍射分析确定了所制备化合物的区域化学。