ethyl 5-amino-3,4-dihydro-4-oxo-3-phenylthieno<3,4-d>pyridazine-1-carboxylate | 123542-47-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩哒嗪类
• 英文名称: ethyl 5-amino-3,4-dihydro-4-oxo-3-phenylthieno<3,4-d>pyridazine-1-carboxylate
• 英文别名: ethyl 5-amino-4-oxo-3-phenyl-3,4-dihydrothieno[3,4-d]pyridazine-1-carboxylate；ethyl 5-amino-3,4-dihydro-4-oxo-3-phenylthieno[3,4-d]pyridazine-1-carboxylate；ethyl 5-amino-6-oxo-1-phenylthieno[3,4-d]pyridazine-3-carboxylate；5-Amino-4-oxo-3-phenyl-3,4-dihydro-thieno[3,4-d]pyridazine-1-carboxylic acid ethyl ester；ethyl 5-amino-4-oxo-3-phenylthieno[3,4-d]pyridazine-1-carboxylate
• CAS: 123542-47-2
• 化学式: C₁₅H₁₃N₃O₃S
• mdl: MFCD00197075
• 分子量: 315.353
• InChiKey: HLVGVGCIJRBRQW-UHFFFAOYSA-N

物化性质

• 熔点：
  191 °C(Solv: 1,4-dioxane (123-91-1); ethanol (64-17-5))
• 沸点：
  517.2±60.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 5-amino-3,4-dihydro-4-oxo-3-phenylthieno<3,4-d>pyridazine-1-carboxylate 在 苄烯丙二腈 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 以36%的产率得到5-氰基-4-甲基-6-氧代-1-苯基-1,6-二氢哒嗪-3-羧酸乙酯
  参考文献：
  名称：

  Elnagdi, Mohamed Hilmy; Negm, Abdalla Mohamed; Erian, Ayman Wahba, Liebigs Annalen der Chemie, 1989, p. 1255 - 1256

  摘要：

  DOI：
• 作为产物：
  描述：

  3-oxo-2-(phenylhydrazono)butyric acid ethyl ester 在 哌啶 、 乙酸铵 、 盐酸 、 sulfur 、 溶剂黄146 作用下， 反应 6.5h， 生成 ethyl 5-amino-3,4-dihydro-4-oxo-3-phenylthieno<3,4-d>pyridazine-1-carboxylate
  参考文献：
  名称：

  Elnagdi, Mohamed Hilmy; Erian, Ayman Wahba; Sadek, Kamal Usef, Journal of Chemical Research, Miniprint, 1990, # 5, p. 1124 - 1142

  摘要：

  DOI：

文献信息

• Synthesis and Studies of Some Nitrogen and Sulfur Compounds
  作者：H. A. Soleiman、F. M. Abd El-Latif、M. A. Khalil、I. H. Elazab

  DOI：10.1080/10426500210672

  日期：2002.4.1

  Pyrazolo-, pyrimidino-, isoxazolo-, thiozolo-, and g -lactam incorporating thienopyridazine has been synthesised by cyclocondensation addition reaction and cycloaddition reaction of hydrazine hydrate phenyl hydrazine, hydroxylamine hydrochloride, urea, thiourea, mercapto acetic acid and monochloroacetyl chloride.

  通过水合肼苯肼、盐酸羟胺、尿素、硫脲、巯基乙酸和一氯乙酰氯的环缩合加成反应和环加成反应，合成了吡唑并、嘧啶基-、异恶唑并、噻唑并和 g-内酰胺并结合了噻吩并哒嗪。
• Studies with condensed aminothiophenes: Further investigation on the reactivity of condensed aminothiophenes toward electron poor and acetylenes under microwave heating
  作者：Balkis Al-Saleh、Morsy A. El-Apasery

  DOI：10.1002/jhet.5570430306

  日期：2006.5

  The reaction of aminothienopyridazines 8a,b, aminothienocoumarin 13 and aminothienonaphthopyran 14 with enaminones 9, 17 and 20a,b under microwave irradiation affords either a mixture of both condensations C-1 alkylation products 15 and 16 or amino moiety alkylation and diethylamine elimination or only one of these products depending on nature of substituents on the thiophene ring. On the other hand

  aminothienopyridazines的反应8A，8B，aminothienocoumarin 13和aminothienonaphthopyran 14与烯胺酮9,17和20A，B在微波辐射下，得到两个都缩合的混合物C-1烷基化产物15和16只有一个或氨基部分烷基化和二乙胺去除或这些产物的种类取决于噻吩环上取代基的性质。另一方面，这些缩合的氨基噻吩与3-二甲基氨基丙烯醛的反应得到24和25。
• Controlled microwave-assisted reactions: A facile synthesis of polyfunctionally substituted phthalazines as dual EGFR and PI3K inhibitors in CNS SNB-75 cell line
  作者：Maiiada Hassan Nazmy、Ramadan Ahmed Mekheimer、Mai E. Shoman、Mohamed Abo-Elsebaa、Mohamed Abd-Elmonem、Kamal Usef Sadek

  DOI：10.1016/j.bioorg.2022.105740

  日期：2022.5

  particular cell line, CNS SNB-75 cell line, but (5b) exhibited the highest growth inhibitory activity against CNS-SNB-75 cell line with (GI% = 108.81) and (IC50 = 3.703 ± 0.2) compared to erlotinib; (IC50 = 12.5 ± 0.68). It caused Pre-G1 apoptosis and growth arrest at S phase. It also increased percentage of the total apoptotic cells in CNS-SNB-75 cell line (39.26%) compared to control cells (2.17%)

  脑肿瘤是顽固的癌症，预后差，存活率令人失望。迫切需要具有更高疗效和更低耐药性的靶向癌症治疗药物。通过将 1-aryl-5-cyano-1,6-dihydro-4-methyl-6-oxo-3-pyridazine-carboxylate 与肉桂腈衍生物的环加成反应，开发了一种高效的多官能化酞嗪衍生物的一锅法合成方法。噻吩并[3,4- d ]哒嗪在受控微波加热下具有高产率的活化双键或三键系统。合成的酞嗪类化合物（5a-e、9和13 ）通过体外试验测试了它们的体外抗癌活性。美国国家癌症研究所的一次剂量测定。只有酞嗪(5b ) 对来自所有子组的大多数测试癌细胞系显示出广谱抗肿瘤活性，平均 % GI = 22.61。有趣的是，所有测试的化合物都对特定细胞系 CNS SNB-75 细胞系表现出不同的生长抑制活性，但 ( 5b ) 对 CNS-SNB-75 细胞系表现出最高的生长抑制活性 (GI% =
• AMINOTHIENOPYRIDAZINE INHIBITORS OF TAU ASSEMBLY
  申请人：Ballatore Carlo

  公开号：US20130029983A1

  公开（公告）日：2013-01-31

  The present invention is directed to methods of inhibiting a tauopathy in a patient by administration of a compound of formula I: Novel aminothienopyridazine compounds are also described.

  本发明涉及通过给予I型化合物来抑制患者的tau病变的方法：还描述了新的氨基噻吩吡嗪化合物。
• A Microwave Assisted Diazo Coupling Reaction: The Synthesis of Alkylazines and Thienopyridazines
  作者：Saleh Al-Mousawi、Abdel-Zaher Elassar、Morsy Ahmed El-Apasery

  DOI：10.1080/10426500500536457

  日期：2006.8.1

  Heating diazoaminobenzene with active methylene compounds 1-3 in microwave oven in acetic acid, in the presence of hydrochloric acid, afforded the corresponding arylhydrazones 5-7. These reaction products were condensed with ethyl cyanoacetate in a domestic microwave oven after 1-2 minutes heating to yield the pyridazinones 8-12. Compounds 8c and 12 reacted with sulfur in basic DMF solution, in microwave oven using MORE technology to yield the thienopyridazinone 14 and 16 respectively. While 17 was produced when 8b was treated like wise with sulfur and DMF in the presence of piperidine. Compounds 16 coupled with aromatic diazonium salts to yield arylazo derivatives 21a-c.