ethyl 4-amino-1-phenyl-1H-pyrazole-3-carboxylate | 1190306-01-4

• 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-1-phenyl-1H-pyrazole-3-carboxylate
• 英文别名: ethyl 4-amino-1-phenylpyrazole-3-carboxylate
• CAS: 1190306-01-4
• 化学式: C₁₂H₁₃N₃O₂
• mdl: MFCD25953513
• 分子量: 231.254
• InChiKey: FROCXJZCPYIFQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 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：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-二氯-1,4-萘醌 、 ethyl 4-amino-1-phenyl-1H-pyrazole-3-carboxylate 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以76%的产率得到ethyl 4-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)-1-phenyl-1H-pyrazol-3-carboxylate
  参考文献：
  名称：

  含吡唑和嘧啶片段的萘醌衍生物的抗惊厥和抗抑郁活性的合成与评价

  摘要：

  通过在2，3-二氯-1，4-萘醌中的氯原子取代为吡唑或嘧啶片段，已经合成了新型杂环二氯萘醌衍生物。这些化合物的结构已通过FT-IR，ESI-MS，1 H-NMR，13 C-NMR和元素分析得到证实。评估合成的化合物在戊四唑（PTZ）惊厥模型中的抗惊厥作用和在强迫游泳试验（FST）中的抗抑郁活性。口服给药后3 h和24 h，所有100 mg / kg的萘醌衍生物均在PTZ诱导的试验中显示出抗惊厥作用。另外，与参考药物阿米替林相比，这些化合物具有延长的抗抑郁特性，从而显着减少了固定时间。

  DOI：

  10.17344/acsi.2020.5938
• 作为产物：
  描述：

  3-ethoxycarbonyl-4-nitro-1-phenylpyrazole 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以90%的产率得到ethyl 4-amino-1-phenyl-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  2-Phenylpyrazolo[4,3-d]pyrimidin-7-one as a New Scaffold To Obtain Potent and Selective Human A₃ Adenosine Receptor Antagonists: New Insights into the Receptor−Antagonist Recognition

  摘要：

  A molecular simplification approach of previously reported 2-arylpyrazolo[3,4-c]quinolin-4-ones was applied to design 2-arylpyrazolo[4,3-d]pyrimidin-7-one derivatives as new human A(3) adenosine receptor antagonists. Substituents with different lipophilicity and steric hindrance were introduced at the 5-position of the bicyclic Scaffold (R-5 = H, Me, Et, Ph, CH2Ph) and on the 2-phenyl ring (OMe, Me). Most of the synthesized derivatives were highly potent hA(3) adenosine receptor antagonists, the best being the 2-(4-methoxyphenyl)pyrazolo[4,3-d]pyrimidin-7-one (K-i = 1.2 nM). The new compounds were also highly selective, being completely devoid of affinity toward hA(1), hA(2A), and hA(2B) adenosine receptors. On the basis of the recently published human A(2A) receptor crystallographic information, we propose it novel receptor-driven hypothesis to explain both A(3) AR affinity and A(3) versus A(2A) Selectivity profiles of these new antagonists.

  DOI：

  10.1021/jm900718w

文献信息

• O-SUBSTITUTED ANILINE DERIVATIVE AND ANTIOXIDANT DRUG
  申请人：NIPPON SODA CO., LTD.

  公开号：EP1944024A1

  公开（公告）日：2008-07-16

  A compound or a salt thereof that exhibits effective antioxidant activity in the treatment of ischemic organ disorders such as arteriosclerosis, myocardial infarction and brain infarction, in the treatment of diseases caused by oxidative cell damage such as renal disease, and in the inhibition of retinal lesions caused by oxidation due to the effects of light or the like. Also provided is an antioxidant drug containing at least one of the compounds or salts as an active ingredient. A compound represented by a formula (1) or a salt thereof, and an antioxidant drug containing at least one of the compound and the salt as an active ingredient. In the formula (1): a represents either 1 or 2, R0 represents an unsubstituted or substituted amino group, R1 to R4 each represent, independently, a hydrogen atom or an alkyl group, E represents an unsubstituted or substituted alkylene chain, D represents a single bond, oxygen atom, unsubstituted or substituted nitrogen atom, sulfur atom, sulfinyl group, sulfonyl group, carbonyl group, carbonylamino group or aminocarbonyl group, and A represents an unsubstituted or substituted aromatic hydrocarbon group, unsubstituted or substituted heterocyclic group, unsubstituted or substituted aralkyl group, or unsubstituted or substituted heteroaralkyl group.}

  一种化合物或其盐，在治疗缺血性器官疾病如动脉硬化、心肌梗死和脑梗死方面表现出有效的抗氧化活性，在治疗由氧化细胞损伤引起的疾病如肾脏疾病方面表现出有效的抗氧化活性，并且在抑制由于光线等的氧化引起的视网膜病变方面表现出有效的抗氧化活性。还提供了一种抗氧化药物，其中包含至少一种该化合物或盐作为活性成分。一种由式（1）表示的化合物或其盐，以及一种抗氧化药物，其中至少包含该化合物和盐中的一种作为活性成分。在式（1）中：a代表1或2，R0代表未取代或取代的氨基团，R1到R4分别独立地代表氢原子或烷基团，E代表未取代或取代的烷基链，D代表单键，氧原子，未取代或取代的氮原子，硫原子，亚砜基，磺酰基，羰基，羰胺基或氨基羰基，A代表未取代或取代的芳香烃基，未取代或取代的杂环基，未取代或取代的芳基烷基，或未取代或取代的杂芳基烷基。}
• HETERO-HALO INHIBITORS OF HISTONE DEACETYLASE
  申请人：Rodin Therapeutics, Inc.

  公开号：US20180194769A1

  公开（公告）日：2018-07-12

  This invention provides compounds that are inhibitors of HDAC2. The compounds (e.g., compounds according to Formula I, II or any of Compounds 100-128 or any of those in Tables 2 or 3) accordingly are useful for treating, alleviating, or preventing a condition in a subject such as a neurological disorder, memory or cognitive function disorder or impairment, extinction learning disorder, fungal disease or infection, inflammatory disease, hematological disease, or neoplastic disease, or for improving memory or treating, alleviating, or preventing memory loss or impairment.
• 2-Phenylpyrazolo[4,3-<i>d</i>]pyrimidin-7-one as a New Scaffold To Obtain Potent and Selective Human A₃ Adenosine Receptor Antagonists: New Insights into the Receptor−Antagonist Recognition
  作者：Ombretta Lenzi、Vittoria Colotta、Daniela Catarzi、Flavia Varano、Daniela Poli、Guido Filacchioni、Katia Varani、Fabrizio Vincenzi、Pier Andrea Borea、Silvia Paoletta、Erika Morizzo、Stefano Moro

  DOI：10.1021/jm900718w

  日期：2009.12.10

  A molecular simplification approach of previously reported 2-arylpyrazolo[3,4-c]quinolin-4-ones was applied to design 2-arylpyrazolo[4,3-d]pyrimidin-7-one derivatives as new human A(3) adenosine receptor antagonists. Substituents with different lipophilicity and steric hindrance were introduced at the 5-position of the bicyclic Scaffold (R-5 = H, Me, Et, Ph, CH2Ph) and on the 2-phenyl ring (OMe, Me). Most of the synthesized derivatives were highly potent hA(3) adenosine receptor antagonists, the best being the 2-(4-methoxyphenyl)pyrazolo[4,3-d]pyrimidin-7-one (K-i = 1.2 nM). The new compounds were also highly selective, being completely devoid of affinity toward hA(1), hA(2A), and hA(2B) adenosine receptors. On the basis of the recently published human A(2A) receptor crystallographic information, we propose it novel receptor-driven hypothesis to explain both A(3) AR affinity and A(3) versus A(2A) Selectivity profiles of these new antagonists.
• Synthesis and Evaluation on Anticonvulsant and Antidepressant Activities of Naphthoquinone Derivatives Containing Pyrazole and Pyrimidine Fragments
  作者：Nataliia Polish、Mariia Nesterkina、Nataliia Marintsova、Andriy Karkhut、Iryna Kravchenko、Volodymyr Novikov、Andrei Khairulin

  DOI：10.17344/acsi.2020.5938

  日期：——

  Synthesized compounds were evaluated for their anticonvulsant action in a pentylenetetrazole (PTZ)-convulsion model and antidepressant activity in the forced swimming test (FST). All naphthoquinone derivatives at a dose 100 mg/kg indicated anticonvulsant effect in PTZ-induced test at 3 h and 24 h after oral administration. In addition, these compounds possessed prolonged antidepressant properties significantly

  通过在2，3-二氯-1，4-萘醌中的氯原子取代为吡唑或嘧啶片段，已经合成了新型杂环二氯萘醌衍生物。这些化合物的结构已通过FT-IR，ESI-MS，1 H-NMR，13 C-NMR和元素分析得到证实。评估合成的化合物在戊四唑（PTZ）惊厥模型中的抗惊厥作用和在强迫游泳试验（FST）中的抗抑郁活性。口服给药后3 h和24 h，所有100 mg / kg的萘醌衍生物均在PTZ诱导的试验中显示出抗惊厥作用。另外，与参考药物阿米替林相比，这些化合物具有延长的抗抑郁特性，从而显着减少了固定时间。