- Improving the Potency of N-Aryl-2,5-dimethylpyrroles against Multidrug-Resistant and Intracellular Mycobacteria
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A series of N-phenyl-2,5-dimethylpyrrole derivatives, designed as hybrids of the antitubercular agents BM212 and SQ109, have been synthesized and evaluated against susceptible and drug-resistant mycobacteria strains. Compound 5d, bearing a cyclohexylmethylene side chain, showed high potency against M. tuberculosis including MDR-TB strains at submicromolar concentrations. The new compound shows bacteriostatic activity and low toxicity and proved to be effective against intracellular mycobacteria too, showing an activity profile similar to isoniazid.
- Touitou, Meir,Manetti, Fabrizio,Ribeiro, Camila Maringolo,Pavan, Fernando Rogerio,Scalacci, Nicolò,Zrebna, Katarina,Begum, Neelu,Semenya, Dorothy,Gupta, Antima,Bhakta, Sanjib,Mchugh, Timothy D.,Senderowitz, Hanoch,Kyriazi, Melina,Castagnolo, Daniele
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p. 638 - 644
(2020/01/11)
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- Double-nitrogen-containing heterocyclic compound and its preparation method and application (by machine translation)
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The invention belongs to the technical field of organic synthesis, and discloses a nitrogen-containing bisheterocyclic compound, and a preparation method and an application thereof. The general formula of the compound is shown in the specification; and in the specification, R1 is H, p-CH3, p-Cl or p-Br, and R2 is H, p-CH3, p-F, 3,4-di-CH3 or p-Br. The preparation method comprises the following steps: reacting a raw material hydrazinobenzene or substituted hydrazinobenzene hydrochloride with acetylacetone to obtain an aryl pyrazole compound b, formylating the compound under Vilsmeier conditions to obtain a 1-aryl-4-pyrazolylaldehyde compound c in a high yield and high selectivity manner, carrying out aldol condensation on the compound c and acetophenone in a EtOH solvent to obtain a chalcone compound d, and carrying out cyclic condensation on the chalcone compound d and hydrazinobenzene or substituted hydrazinobenzene hydrochloride in the EtOH solvent to obtain the nitrogen-containing bisheterocyclic compound e. The preparation method has the advantages of simple process, mild reaction conditions, high yield, easy post-treatment, maneuverability, and suitableness for large scale preparation.
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- Reactions of 3,5-dimethyl-1-phenyl-1h-pyrazole with electrophiles
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Reactions of 3,5-dimethyl-1-phenyl-1H-pyrazole with various electrophilic reagents were studied. Electrophilic attack occurred regioselectively at the C4 atom in the pyrazole ring. Pleiades Publishing, Ltd., 2012.
- Attaryan,Rstakyan,Hasratyan
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p. 1724 - 1727
(2013/02/23)
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- Synthesis and antimicrobial activity of linked heterocyclics containing pyrazole-pyrimidine rings
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New series of 4-(aryl/hetaryl)-6-(3,5-dimethyl-1-phenyl-1H-4-pyrazolyl)-2- pyrimidinamine 5a-j has been prepared and confirmed by IR, NMR, MS and elemental analyses. All the synthesized compounds have been tested for their antimicrobial activity against bacteria and fungi. Among the synthesized compounds, the compounds containing 4-nitrophenyl 5c, 2-furyl 5h and 2-thiazolyl 5j at 6-position of pyrimidine ring are highly active against all the organisms employed.
- Sanjeeva Reddy,Vani Devia,Rajesh Kumara,Sanjeeva Raoa,Nagarajb
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p. 1181 - 1186
(2011/10/12)
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- Synthesis of novel linked pyrazolyl-thiazolidinone heterocycles as potent antibacterial agents
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A novel series of 2-(3,5-dimethyl-1-phenyl-1H-4-pyrazolyl)-3-(aryl/ heteroaryl)-1,3-thiazolidin-4-one derivatives 4a-h has been synthesized readily in one-pot from 3,5-dimethyl-1-phenyl-1H-4-pyrazolecarbaldehyde (3), and characterized via IR, NMR, MS and elemental analyses. Further, these compounds were screened for antibacterial (MIC) activity against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Staphylococcus pyogenes. Amongst them, compounds containing pyridyl 4g and pyrimidinyl 4h moiety exerted superior antibacterial activity against S. aureus and E. coli at the concentration of 6.25 μg/mL, which is less than the concentration of the standards neomycin and streptomycin, and emerged as potential molecules for further development.
- Reddy, Cherkupally Sanjeeva,Kumar, Gaddam Rajesh,Devi, MacHerla Vani,Nagaraj, Adki
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p. 576 - 581
(2012/04/18)
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- Synthesis and antimicrobial study of linked heterocyclics containing pyrazole-pyrimidine-thiazolidin-4-one
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A new series of linked heterocyclics, 3-[4-(4-chlorophenyl)-6-(3,5- dimethyl-1-phenyl-1H-4-pyrazolyl)-2-pyrimidinyl]-2-(aryl/heteryl)-1, 3-thiazolan-4-ones (6a - j), has been synthesized by the one-pot cyclo-condensation of 4-(4-chlorophenyl)-6-(3,5-dimethyl-1-phenyl-1H-4- pyrazolyl)-2-pyrimidinamine (5), aryl/heteroaryl aldehyde and thioglycolic acid. The structures of the synthesized compounds have been confirmed via IR, 1H-NMR, 13C-NMR, MS and elemental analyses. Further, all the newly synthesized compounds 6a - j have been assayed for their antimicrobial activity against Gram-positive and Gram-negative bacteria and fungi. The compounds containing moieties like 4-nitrophenyl (6c), 3-nitrophenyl (6d), 4-dimethylaminophenyl (6g), 2-furyl (6i) and 1,3-benzodioxole (6j), at 2-position of thiazolidin-4-one ring exhibited good inhibitory activity against all the tested organisms.
- Sanjeeva Reddy, Cherkupally,Vani Devi, Macherla,Sunitha, Malladi,Nagaraj, Adki
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experimental part
p. 1622 - 1626
(2011/02/22)
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- An efficient synthesis of radiolabelled SANT-1
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SANT-1, (4-benzyl-N-[(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)methylene]-1- piperazinamine), is a reference compound and used for establishing a biological assay for the smoothened receptor (SMO). Preparation of radiolabelled material was needed for establishing radioligand protein/receptor binding studies. [ 3H]SANT-1 was prepared with a radiochemical purity of >95% (25 Ci/mmol) using direct Crabtree catalyzed T/H exchange method, while [ 14C]SANT-1 was synthesized at 98.2% radiochemical purity (54 mCi/mmol) using [14C]dimethylformamide. The details of the syntheses of radioactive labelled SANT-1 were presented. Copyright
- Zhang, Yinsheng,Stolle, Wayne T.
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scheme or table
p. 487 - 489
(2011/05/05)
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- Routes to building blocks for heterocyclic synthesis by reduction of ketene dithioacetals
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Two general methods have been developed permitting the effective reduction of ketene dithioacetals to give substituted dithianes. Reduction with magnesium in methanol is less reliable than reduction with zinc in acetic acid. The greater inconsistency of magnesium in methanol has been investigated by a cyclic voltammetric study of the substrates. The utility of the dithianes has been successfully illustrated by cyclisations to afford, after deprotection, a variety of heterocyclic aldehydes.
- Mellor, John M.,Schofield, Stephen R.,Korn, Stewart R.
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p. 17151 - 17162
(2007/10/03)
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- Research in the Azole Series. Synthesis and 13C NMR Study of Pyrazole-4-carboxaldehydes
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Ten new pyrazoles have been prepared and their 13C nmr chemical shifts compared with those of twelve other pyrazoles, some of them prepared purposely for this study.The chemical shifts are discussed statistically assuming that they are additive.A formyl group in the position 4 of the pyrazole ring produces a large effect on carbon C4 (SCS = 17.3 ppm) and medium effects on carbons C3 (SCS = 1.9 ppm) and C5 (SCS = 3.8 ppm).The azines derived from pyrazole-4-carboxaldehydes are of the E,E-configuration.
- Echevarria, Aurea,Elguero, Jose,Meutermans, Wim
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p. 957 - 960
(2007/10/02)
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- Synthese regiospecifique d'acyl-4 pyrazoles a partir d'acyl-5 pyrimidines
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The transformation of variously substituted 5-acetyl-4-methylpyrimidines 1 into 4-acetyl-1-amidino-3-methylpyrazole amidinohydrazone dihydrochloride 3, under the action of amidinohydrazine hydrochloride, in boiling acidic methanolic solution, depends on the nature of the 2-substituent of pyrimidines 1, and on the stability of the amidinohydrazone of pyrimidines 2 under the reaction conditions.Phenylhydrazine transforms all the pyrimidines 1 into pyrazoles, regiospecifically or not, according to the nature of the 2-substituent of pyrimidines 1.This new possibility of ring contraction has been extended to other unsymetrical 5-acyl- and 5-ethoxycarbonylpyrimidines.
- Bajnati, Abdelilah,Kokel, Bruno,Hubert-Habart, Michel
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p. 318 - 324
(2007/10/02)
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- Pyrazol-4-acetic acid compounds
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Pyrazol-4-acetic acid compounds, such as substituted pyrazol-4-acetic acid, its esters, amides, nitriles and their pharamaceutically acceptable salts and method for the preparation of these compounds are disclosed. The novel compounds are useful analgesics, anti-inflammatory, and antipyretics.
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