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Phthalazinopyrrole compound and preparation method thereof

A compound and a technology for a synthesis method are applied in the field of phthalazinopyrrole compounds and their preparation, and achieve the effects of easy separation and purification, fast reaction speed and few side reactions

Active Publication Date: 2016-06-15
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Phthalazinoheterocyclic compounds are also a class of heterocyclic molecules with biological activity, and their high antiepileptic activity has been extensively studied, and there have been many reports on the synthesis methods of phthalazinoheterocyclic compounds (Arzneimittelforschung.2010, 60 (6): 289-92.; Eur.J.Med.Chem.2010, 45(11):4807-12.; ChemBiolDragDes.2009, 73, 313-319.; AsianJournalofChemistry.2011, 24, 127-131. ; J.Org.Chem., 2011, 76:7730-7736), but there are few reports on the mild and efficient synthesis of phthalazinopyrrole heterocyclic compounds

Method used

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  • Phthalazinopyrrole compound and preparation method thereof
  • Phthalazinopyrrole compound and preparation method thereof
  • Phthalazinopyrrole compound and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] Put 0.0388g (0.2mmol) of compound 1a, 0.0607g (0.3mmol) of compound 2a and 1mL of dichloromethane into a dry 15mL Shrek tube, add 10.6mg (0.04mmol) of triphenylphosphine and mix well for cycloaddition into a reaction. In this reaction system, the molar ratio of Compound 1a to Compound 2a is 1:1.5, the organophosphorus catalyst accounts for 20% of the molar percentage of Compound 1a, stirred at 25° C. for 48 hours, concentrated through a column with a rotary evaporator (ethyl acetate Ester: Petroleum ether = 1:5, v / v), to obtain 63.4 mg of product 3aa, with a yield of 80%.

Embodiment 2

[0029]

[0030] Put 0.0388g (0.2mmol) of compound 1a, 0.0607g (0.3mmol) of compound 2a and 1mL of dichloromethane into a dry 15mL Shrek tube, add 0.04mmol of trimethylphosphine and mix well for cycloaddition reaction. In this reaction system, the molar ratio of compound 1a to compound 2a is 1: 1.5, the organophosphorus catalyst accounts for 20% of the molar percentage of compound 1a, stirred at 25°C for 2 hours, concentrated through a column with a rotary evaporator (ethyl acetate Ester:petroleum ether=1:5, v / v), to obtain 67.4mg of product 3aa, yield 85%.

Embodiment 3

[0032]

[0033] Put 0.0388g (0.2mmol) of compound 1a, 0.0607g (0.3mmol) of compound 2a and 1mL of dichloromethane into a dry 15mL Shrek tube, add 0.04mmol of dimethylphenylphosphine and mix well for cycloaddition reaction . In this reaction system, the molar ratio of compound 1a to compound 2a is 1: 1.5, the organophosphorus catalyst accounts for 20% of the molar percentage of compound 1a, stirred at 25°C for 2 hours, concentrated through a column with a rotary evaporator (ethyl acetate Ester:petroleum ether=1:5, v / v), to obtain 75.3mg of product 3aa, yield 95%.

[0034] It can be seen that the effect is very excellent when dimethylphenylphosphine is selected as the catalyst.

[0035] 3aa NMR

[0036] 1 HNMR (300MHz, CDCl 3)δ7.81(s, 1H), 7.50(td, J=7.4, 1.5Hz, 1H), 7.46-7.40(m, 1H), 7.39-7.31(m, 3H), 7.30-7.24(m, 1H) , 7.23-7.18(m, 2H), 7.11(d, J=7.4Hz, 1H), 4.54-4.23(m, 3H), 3.90(q, J=15.4Hz, 2H), 3.36(dd, J=16.4 , 5.8Hz, 1H), 3.04(ddd, J=16.4, 10.2, 1.4Hz, 1H), 1.37...

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Abstract

The invention discloses a phthalazinopyrrole compound and a preparation method thereof. The phthalazinopyrrole compound has potential antibacterial, anti-inflammatory and anti-tumour activities. The preparation method of the compound comprises the following steps: under the nitrogen protection condition, dissolving phthalazine derived 1,3-dipole and allene ester into an organic solvent, adding an organic phosphine catalyst, stirring, and carrying out cycloaddition reaction, so that the phthalazinopyrrole compound can be obtained.

Description

technical field [0001] The invention relates to a class of phthalazinopyrrole compounds and a preparation method thereof. Background technique [0002] Phthalazine compounds are a class of nitrogen-containing heterocyclic compounds with good biological activity, which have various pharmacological effects such as antihistamine, antibacterial, anti-inflammatory, and antitumor (Arch.Pharm.1988, 324, 205-208. ; PhOSPHORUSSULFUR.2005, 180, 1997-2011.; Chem.Abstr.2000, 133, 29641), wherein the aniline phthalazine compound PTK787 is in the clinical trial stage, mainly used for the treatment of prostate cancer, colon cancer and kidney cancer, clinical Dihydralazine used on the Internet can be used to treat hypertension and refractory heart failure. Phthalazinoheterocyclic compounds are also a class of heterocyclic molecules with biological activity, and their high antiepileptic activity has been extensively studied, and there have been many reports on the synthesis methods of phtha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04B01J31/24
CPCB01J31/2404B01J2231/324C07D487/04
Inventor 郭红超袁春浩周磊杰王昌高阵阵
Owner CHINA AGRI UNIV
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