ethyl 4-amino-3-(4-chlorophenyl)-1H-pyrazol-5-carboxylate | 91857-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-amino-3-(4-chlorophenyl)-1H-pyrazol-5-carboxylate
• 英文别名: ethyl 4-amino-3-(4-chlorophenyl)-1H-pyrazole-5-carboxylate
• CAS: 91857-59-9
• 化学式: C₁₂H₁₂ClN₃O₂
• 分子量: 265.699
• InChiKey: ZSQNIFUXLRKJNU-UHFFFAOYSA-N

物化性质

• 沸点：
  476.1±45.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  81
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-amino-3-(4-chlorophenyl)-1H-pyrazol-5-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以70%的产率得到4-amino-3-(4-chlorophenyl)-1H-pyrazol-5-carbohydrazide
  参考文献：
  名称：

  具有氧杂/噻二唑基，吡唑基部分和吡唑并[4,3- d ]-嘧啶衍生物的新型吡唑衍生物作为潜在的抗微生物剂和抗癌剂

  摘要：

  一系列的[4-氨基-3-（4-氯苯基）-1 H-吡唑-5-基]（3,5-二甲基-1 H-吡唑-1-基）-甲酮和6-氨基-3- （4-氯苯基）-5-甲基-1,6-二氢-7 H-吡唑并[4,3 - d ]-嘧啶-7-是由乙基4-氨基-3-（4-氯苯基）-合成的吡唑-5-羧酸盐。通过IR，1 H NMR，13 CNMR，质谱和元素分析对新合成的化合物进行表征。评价化合物的体外抗微生物和抗癌活性。在合成的化合物中，化合物7a，b和15与参考药物阿霉素相比，具有更高的抗癌活性。大多数新合成的化合物都具有良好的抗菌性能。

  DOI：

  10.1016/j.bmcl.2016.03.117
• 作为产物：
  描述：

  4-(4-氯苯基)-2,4-二氧代丁酸乙酯 在 盐酸 、 hydrazine hydrate 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 7.0h， 生成 ethyl 4-amino-3-(4-chlorophenyl)-1H-pyrazol-5-carboxylate
  参考文献：
  名称：

  合成新的吡唑并[4,3-d]嘧啶-7-酮和吡啶并[2,3-d]嘧啶-4-酮具有抑制细菌和细胞周期蛋白依赖性激酶（CDKs）的活性

  摘要：

  设计，合成并合成了两个系列的吡唑并[4,3-d]嘧啶-7-酮和吡啶并[2,3-d]嘧啶-4-酮，并评估了它们的抗菌活性和CDKs抑制活性。哒嗪衍生物：6-苯基-5-苯基肼基-2,3,4,5-四氢哒嗪-3,4-二酮（3a）表现出对金黄色葡萄球菌革兰氏阳性菌的活性，而化合物2-（2-乙氧基苯基-5） -苯基哌嗪基磺酰胺基）-3H-吡啶并[2,3-d]嘧啶-4-酮（13c）对白念珠菌具有中等程度的抗真菌活性。

  DOI：

  10.1007/s00044-010-9328-z

文献信息

• Synthesis and Biological Evaluation of N- Pyrazolyl Derivatives and Pyrazolopyrimidine Bearing a Biologically Active Sulfonamide Moiety as Potential Antimicrobial Agent
  作者：Hend Hafez、Abdel-Rhman El-Gazzar

  DOI：10.3390/molecules21091156

  日期：——

  A series of novel pyrazole-5-carboxylate containing N-triazole derivatives 3,4; different heterocyclic amines 7a-b and 10a-b; pyrazolo[4,3-d]pyrimidine containing sulfa drugs 14a,b; and oxypyrazolo[4,3-d]pyrimidine derivatives 17, 19, 21 has been synthesized. The structure of the newly synthesized compounds was elucidated on the basis of analytical and spectral analyses. All compounds have been screened

  一系列含有N-三唑衍生物3,4的新颖的吡唑-5-羧酸盐；不同的杂环胺7a-b和10a-b；含吡唑并[4，3-d]嘧啶的磺胺药物14a，b；合成了吡唑并[4，3-d]嘧啶衍生物17、19、21。在分析和光谱分析的基础上阐明了新合成化合物的结构。筛选了所有化合物对三种革兰氏阳性和革兰氏阴性细菌以及三种真菌的体外抗菌活性。结果表明，化合物14b和17对所有细菌菌株的抗菌作用均强于参比药物头孢噻肟。此外化合物4、7b，
• First synthesis of arylpyrrolo- and pyrazolopyrrolizinones as useful agents with potential biological interest
  作者：Christophe Rochais、Vincent Lisowski、Patrick Dallemagne、Sylvain Rault

  DOI：10.1016/j.tetlet.2004.06.047

  日期：2004.8

  three or four steps starting from aminoarylpyrrole and pyrazole carboxylates through the cyclisation of a Vilsmeier–Haack intermediate. This synthesis was enhanced by diverse N-protections of the aza-heterocycle and furnish new series with potential biological interest.

  新型芳基吡咯并吡咯并吡咯并吡嗪酮是通过三步或四步制备的，从氨基芳基吡咯和吡唑羧酸酯开始，通过Vilsmeier-Haack中间体的环化反应。通过氮杂杂环的各种N-保护增强了该合成，并提供了具有潜在生物学意义的新系列。
• Novel 6-N-arylcarboxamidopyrazolo[4,3-d]pyrimidin-7-one derivatives as potential anti-cancer agents
  作者：Vani N. Devegowda、Jung Hyun Kim、Ki-Cheol Han、Eun Gyeong Yang、Hyunah Choo、Ae Nim Pae、Ghilsoo Nam、Kyung Il Choi

  DOI：10.1016/j.bmcl.2010.01.029

  日期：2010.3

  A novel series of 3,5,6-trisubstituted pyrazolo[4,3-d] pyrimidin-7-one derivatives, especially 6-N-arylcarboxamidopyrazolo[4,3-d]pyrimidin-7-ones were synthesized and evaluated for their in vitro anticancer activities against various human cancer cell lines. The inhibitory activities for several kinases have also been tested. The prepared compounds library exhibited significant anticancer activity towards HT-29 colon and DU-145 prostate cancer cell lines. The structure-activity relationships of the 6-N-arylcarboxamidopyrazolo[4,3-d] pyrimidin-7-one scaffold at R-1, R-2 and R-3 have been elucidated. Among the synthesized compounds, 12b was the most active compound with GI(50) value of 0.44 mu M and 1.07 mu M against HT-29 and DU-145 cell lines, respectively, and 13a was the most selective compound towards colon cancer cell line. (C) 2010 Published by Elsevier Ltd.
• Synthesis of Novel Pyrazolopyrrolizinones as Prospective Anticancer Agents
  作者：Christophe Rochais、Patrick Dallemagne、Sylvain Rault、Jana Sopkovà-de Oliveira Santos

  DOI：10.3987/com-06-10824

  日期：——

  Herein we describe the access of novel pyrazolopyrrolizinones from commercial arylacetonitriles. The first step conducts to the corresponding aminoester which was first submitted to Clauson-Kaas procedure. Amidification and cyclisation afford then the first examples of the expected heterocycles. In order to improve the sequence and to obtain N-substituted isomers, 3-aryl-5-(pyrrolidin-1-ylcarbonyl)-4-(1H-pyrrol-1-yl)-1H-pyrazoles (5) were alkylated and conduct to two different N-substituted pyrazoles. These novel products were separated by chromatography and clearly identified using different analytical techniques. Application of the cyclisation procedure conducts then to the two corresponding final title products.
• Tarzia; Panzone; de Paoli, Farmaco, Edizione Scientifica, 1984, vol. 39, # 7, p. 618 - 636
  作者：Tarzia、Panzone、de Paoli、Schiatti、Selva

  DOI：——

  日期：——