4,5-dihydro-6-(naphthalen-2-yl)-4-phenyl-2H-indazol-3-ol | 1276692-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,5-dihydro-6-(naphthalen-2-yl)-4-phenyl-2H-indazol-3-ol
• 英文别名: 6-(2-naphthyl)-4-phenyl-4,5-dihydro-2H-indazol-3-ol；6-naphthalen-2-yl-4-phenyl-1,2,4,5-tetrahydroindazol-3-one
• CAS: 1276692-03-5
• 化学式: C₂₃H₁₈N₂O
• 分子量: 338.409
• InChiKey: LQCMNNZRZDHQFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(naphthalen-2-yl)-3-phenylprop-2-en-1-one 在 sodium 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4,5-dihydro-6-(naphthalen-2-yl)-4-phenyl-2H-indazol-3-ol
  参考文献：
  名称：

  Synthesis and antimicrobial activities of new 4,6-diaryl- 4,5-dihydro-3-hydroxy-2H-indazoles

  摘要：

  AbstractA series of new 4,6‐diaryl‐4,5‐dihydro‐3‐hydroxy‐2H‐indazoles 5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j, 5k were synthesized by the cyclization of ethyl 2‐oxo‐4,6‐diarylcyclohex‐3‐ene carboxylates 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k. The compounds were characterized by IR, 1H NMR, 13C NMR, 2D NMR, and elemental analysis. The synthesized compounds were evaluated for in vitro antibacterial and antifungal activities against Staphylococcus aureus, Escherichia coli, Salmonella typhimurium, Pseudomonas aeruginosa, Candida albicans, Aspergillus niger, Aspergillus flavus, and Rhizopus sp. Most of the compounds exhibited good activity against the tested organisms. J. Heterocyclic Chem.,, (2012).

  DOI：

  10.1002/jhet.720

文献信息

• Antimicrobial Activities of some Synthesized Pyridines, Oxazines and Thiazoles from 3-Aryl-1-(2-naphthyl)prop-2-en-1-ones
  作者：Salwa Mohamed

  DOI：10.3797/scipharm.0804-09

  日期：——

  3-Aryl-1-(2-naphthyl)-prop-2-en-1-ones were reacted with ethyl cyanoacetate to produce 4-aryl-6-(2-naphthyl)-2-oxo-1,2-dihydropyridine-3-carbonitriles, which were treated with ethyl chloroacetate to give the corresponding ester. Treatment of the latter ester with hydrazine hydrate or anthranilic acid afforded hydrazides and benzoxazines. The hydrazides were reacted with benzaldehyde or phenylisothiocyanate to afford the corresponding hydrazone and thiosemicarbazide derivatives, which were cyclized with chloroacetic acid or thioglycolic acid to the corresponding thiazole derivatives. 3-Aryl-1-(2-naphthyl)-prop-2-en-1-ones were either condensed with malononitrile under different conditions to produce carbonitrile derivatives or treated with active methylene reagents to afford the substituted cyclohexene derivatives. The structure assignment of the new compounds is based on chemical and spectroscopic evidence. Some of these compounds exhibited antimicrobial activities comparable to Ampicillin® as reference drug.

  3-芳基-1-(2-萘基)-丙-2-烯-1-酮与乙基氰乙酸酯反应，生成4-芳基-6-(2-萘基)-2-氧-1,2-二氢吡啶-3-氰基，随后与乙基氯乙酸酯处理以得到相应的酯。将后续酯与水合肼或邻氨基苯甲酸处理，得到肼和苯并噁唑衍生物。这些肼与苯甲醛或苯异硫氰酸酯反应，得到相应的肼亚胺和噻唑半卡巴肟衍生物，然后与氯乙酸或硫醇酸环化，生成相应的噻唑衍生物。3-芳基-1-(2-萘基)-丙-2-烯-1-酮在不同条件下与马隆腈缩合生成氰基衍生物，或与活性亚甲基试剂反应生成取代的环己烯衍生物。新化合物的结构指派基于化学和光谱证据。这些化合物中的一些显示出与阿莫西林®相当的抗微生物活性。
• Synthesis, spectral analysis and <i>in vitro</i> microbiological evaluation of novel ethyl 4-(naphthalen-2-yl)-2-oxo-6-arylcyclohex-3-enecarboxylates and 4,5-dihydro-6-(napthalen-2-yl)-4-aryl-2<i>H</i>-indazol-3-ols
  作者：V. Kanagarajan、J. Thanusu、M. Gopalakrishnan

  DOI：10.3109/14756361003689856

  日期：2011.2.1

  A series of ethyl 4-(naphthalen-2-yl)-2-oxo-6-arylcyclohex-3-enecarboxylates 8--14 and 4,5-dihydro-6-(naphthalen-2-yl)-4-aryl-2H-indazol-3-ols 15--21 were synthesised and characterised by their spectroscopic data. In vitro microbiological evaluations were carried out for all the newly synthesised compounds 8--21 against clinically isolated bacterial and fungal strains. Compounds 9, 12 and 20 against Staphylococcus aureus, 10, 12, 20 against beta beta-haemolytic streptococcus, 11, 17 against Bacillus subtilis, 12, 16 and 20 against Vibreo cholerae, 13, 16 against Escherichia coli, 13, 16, 18, 19 against Salmonella typhii, 12, 18 against Shigella flexneri, 10 against Salmonella typhii, 10, 13, 17, 18 against Aspergillus flavus, 12, 17, 21 against Aspergillus niger, 12, 15, 17, 18, 20 against Mucor, Rhizopus and Microsporeum gypsuem exhibit potent antimicrobial activity.
• Synthesis and antimicrobial activities of new 4,6-diaryl- 4,5-dihydro-3-hydroxy-2H-indazoles
  作者：Parasuraman Amutha、Samuthira Nagarajan

  DOI：10.1002/jhet.720

  日期：2012.3

  AbstractA series of new 4,6‐diaryl‐4,5‐dihydro‐3‐hydroxy‐2H‐indazoles 5a, 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 5j, 5k were synthesized by the cyclization of ethyl 2‐oxo‐4,6‐diarylcyclohex‐3‐ene carboxylates 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j, 4k. The compounds were characterized by IR, 1H NMR, 13C NMR, 2D NMR, and elemental analysis. The synthesized compounds were evaluated for in vitro antibacterial and antifungal activities against Staphylococcus aureus, Escherichia coli, Salmonella typhimurium, Pseudomonas aeruginosa, Candida albicans, Aspergillus niger, Aspergillus flavus, and Rhizopus sp. Most of the compounds exhibited good activity against the tested organisms. J. Heterocyclic Chem.,, (2012).