Antimycobacterial activity of new ortho-, meta- and para-toluidine derivatives

Biava, Mariangela; Fioravanti, Rossella; Porretta, Giulio Cesare; Sleiter, G.; Deidda, Delia; Lampis, Giorgio; Pompei, Raffaello

doi:10.1016/s0014-827x(99)00084-1

Cited by 18 publications

(27 citation statements)

References 9 publications

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“…NHBenzotriazole displayed poor reactivity, as the N-alkylated products 15-17 were isolated in moderate to low yields. In the case of 5-methylbenzo [1,2,3]triazole, the product was isolated as mixture of two regioisomers 17a and 17b in 55:45 ratio. Finally, our catalytic system displayed similar performance than other protocols [19a] for the N-alkylation of sulfonamides, as 18 and 19 were obtained in 96% and 86% yields.…”

Section: Resultsmentioning

confidence: 99%

“…138.6, 132.5, 125.8, 124.0, 121.2, 120.4, 109.2, 58.2, 32.5, 25.9, 25.5 [d][1,2,3]triazole (15). Following the general procedure using NH-benzo [d] [1,2,3]triazole (60 mg, 0.5 mmol) and cyclohexane (3 mL), 15 was isolated in 35% yield (35 mg) as a light yellow oil after purification using flash column chromatography with pentane : ethyl acetate = 40 : 1. 1 34 (m, 5H).…”

Section: N-cyclohexylindazole (14)mentioning

confidence: 99%

“…13 C NMR (101 MHz, CDCl3) δ (ppm) 146. 1, 132.2, 126.7, 123.7, 120.1, 109.8, 59.1, 32.6, 25.6, 25.3 4, 136.9, 133.4, 131.2, 119.1, 109.3, 58.9, 32.5, 25.6, 25.3, 20.9, 20.4 [1,2,3]triazole (74 mg, 0.5 mmol) and cyclohexane (3 mL), 17a and 17b was isolated in 41% yield (44 mg) in 45:55 ratio as a light yellow oil after purification using flash column chromatography with pentane : ethyl acetate = 40 : 1. 1 H NMR (300 MHz, CDCl3) δ (ppm) 7.92 (d, J = 8.5 Hz, 1H, 17b), 7.81 (s, 1H, 17a), 7.46 (d, J = 8.5 Hz, 1H, 17a), 7.34 (s, 1H, 17b), 1H,17a),7.17 (dd,J = 1.4,8.5 Hz,1H,17b),1H,17a+17b), 2.54 (s, 3H, 17b), 2.51 (s, 3H, 17a), 2.23 -2.09 (m, 4H, 17a+17b), 2.08 -1.92 (m, 2H, 17a+17b), 1.87 -1.75 (m, 1H, 17a+17b), 1.61 -1.46 (m, 2H, 17a+17b), 1.45 -1.33 (m, 1H, 17a+17b).…”

Section: N-cyclohexylindazole (14)mentioning

confidence: 99%

“…[2] The N-cycloalkyl pyrrole II is an analogue of BN1212 exhibiting antitubercular properties. [3] The N-cyclopentylindazole III was used as a selective inhibitor of EZH2. [4] The N- (tert-butoxymethyl)indole IV has shown inhibition properties on vascular endothelial growth factors, which are important signaling proteins involved in both vasculogenesis and angiogenesis ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%

“…[18] Outstanding achievements are emerging in this area [19] although only amines with low nucleophilicity were successfully alkylated. For example, Hartwig and co-workers reported C(sp 3 )-H amination of cyclohexane with phthalimide and sulfonamides. [19c] Cai and co-workers have reported that with NH-indole, using nickel catalyst, regiospecific C2-or C3-products were obtained without the formation of N-alkylated indole (Figure 2c).…”

Section: Introductionmentioning

confidence: 99%

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Copper‐Catalyzed Oxidative Dehydrogenative C(sp³)−H Bond Amination of (Cyclo)Alkanes using NH‐Heterocycles as Amine Sources

Wang

Dixneuf

et al. 2017

ChemSusChem

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A copper-catalyzed oxidative C(sp 3 )-H/N-H coupling of NH-heterocycles with affordable (cyclo)alkanes was developed. This protocol involved C(sp 3 )-N bond formation via a radical pathway generated by a homolytic cleavage of di-tert-butyl peroxide and trapping of the radical(s) by copper catalysts. The reaction tolerated a series of functional groups, such as bromo, fluoro, ester, ketone, nitrile, methyl and methoxy. NH-free indoles, pyroles, pyrazoles, indazoles and benzotriazoles have been successfully N-alkylated.

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Section: Resultsmentioning

confidence: 99%

Section: N-cyclohexylindazole (14)mentioning

confidence: 99%

Section: N-cyclohexylindazole (14)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Copper‐Catalyzed Oxidative Dehydrogenative C(sp³)−H Bond Amination of (Cyclo)Alkanes using NH‐Heterocycles as Amine Sources

Wang

Dixneuf

et al. 2017

ChemSusChem

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ChemInform Abstract: Antimycobacterial Activity of New ortho‐, meta‐, and para‐Toluidine Derivatives.

et al. 2000

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Synthesis and Antimicrobial Activity of 2‐Methyl‐5‐nitroaniline Derivatives: A Structure‐Activity Relationship Study

et al. 2011

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R ECE t a b r ~ JAN 0 5 1.995 1. SYNTHESIS AND 8ECEPTOR AFFINITIES OF NEW 3-QUINUCLIDINYL ALPHA-HETEROARYL-ALPHA-ARYL-ALPHA-HYDROXYACETATES (see Schemes in App. 1.1). Five analogues of 3-quinuclidinyl benzilate were prepared in which one phenyl ring was substituted by a heterocycle; a bromine was included on either the remaining phenyl or t h e heterocycle to provide information relating to the affinity of potential radiohalogenated derivatives. The required methyl 4-bromophenylglyoxalate (1) was synthesized from t h e reaction between 4-bromophenylmagnesium bromide with an excess of dimethyl oxalate a t-700 C. The reaction between ethyl oxalyl chloride with 2-bromothiphene provides ethyl 2-(5-bromothienyl)glyoxatate (2). Compounds (1) and (2) react with an equivalent amount of Grignard reagent to provide methyl or ethyl alpha-aryl-alpha-heteroarylglycolates (3). Transesterification of t h e methyl or ethyl esters (3) with (R,S)-3-quinuclidinol (4) in t h e presence of sodium metal provides t h e final products (5). A s a result of screening the novel compounds, we found a heterocyclic derivative of QNB that may surpass IQNB as a CNS receptor radioligand. This novel compound binds to mAChRs with an affinity that is greater than that of IQNB, i5 selective for the m l subtype, and is less lipophilic than IQNB, which should reduce t h e serum proteip binding relative to IQNB.[ [ [ (D I A LKY LA M I N 0) ALKYL]-1-PIPE RI D I N Y L] ACETYL]-1 0,l 1-D I HY D RO-5 H-D I B E N 20 [ b, e] [ 1,4] DIAZEPIN-1 1-ONES AS rn2-SELECTIVE ANTlMUSCARlNlCS (see Schemes in App. 1.2). The required 1 1-oxo-1 0,l 1-dihydro-5H-dibenzo[b,e] [1,4]diazepine (9) was prepared from the reaction between 2-chlorobenzoic acid and o-phenylenediamine. The reaction between 2-and 4-vinylpyridines (5 a , b) and dialkylamines (6a-e) provided 2-and 4-(dialkylamino)ethylpyridines (7). 4-Picolyllithium '(5~) reacted with 3-(dimethyl-or diethy1amino)propyl chloride to provide 4-[4-(dimethyl-or diethylamino) butyllpyridines (7). [(Dialkylamino)alkyl]pyridines-(7) were converted into the respective piperidines (8) by catalytic reduction(p1atinum oxide). Condensation of the tricycle (9) with chlocoacetyl chloride provided 5-(chloroacety1)-1 0,l 1-dihydro-SH-d i b e n z o [ b , e ] [ 1 , 4 ] d i a z e p i n-1 l-o n e (1 0). S u b s e q u e n t r e a c t i o n with [(dialkylamino)alkyl]piperidines (8) yielded t h e final products (4)-Compounds (4a-g,iIj) and two reference compounds (Table 111 in App. 1.2) were tested for their apparent affinities for the m l and m2 subtypes. Table 111 compares the selectivity and potency of these compounds to other compounds. These data demonstrate that (4j) is t h e most potent compound in the series. This compound is selective for m2 receptors over ml receptors by approximately 8-fold. These results also demonstrate t h a t (41) is approxhately 1 0 times more potent a t m2 receptors than AQ-RA 741. However, (4j) does not significantly penetrate the BBB. Cohen, Baumgold, Jin, de la Cruz, Rzeszotarski, Reba, J. Med. Chem. 36, ...

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Antimycobacterial activity of new ortho-, meta- and para-toluidine derivatives

Cited by 18 publications

References 9 publications

Copper‐Catalyzed Oxidative Dehydrogenative C(sp³)−H Bond Amination of (Cyclo)Alkanes using NH‐Heterocycles as Amine Sources

Copper‐Catalyzed Oxidative Dehydrogenative C(sp³)−H Bond Amination of (Cyclo)Alkanes using NH‐Heterocycles as Amine Sources

ChemInform Abstract: Antimycobacterial Activity of New ortho‐, meta‐, and para‐Toluidine Derivatives.

Synthesis and Antimicrobial Activity of 2‐Methyl‐5‐nitroaniline Derivatives: A Structure‐Activity Relationship Study

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Antimycobacterial activity of new ortho-, meta- and para-toluidine derivatives

Cited by 18 publications

References 9 publications

Copper‐Catalyzed Oxidative Dehydrogenative C(sp3)−H Bond Amination of (Cyclo)Alkanes using NH‐Heterocycles as Amine Sources

Copper‐Catalyzed Oxidative Dehydrogenative C(sp3)−H Bond Amination of (Cyclo)Alkanes using NH‐Heterocycles as Amine Sources

ChemInform Abstract: Antimycobacterial Activity of New ortho‐, meta‐, and para‐Toluidine Derivatives.

Synthesis and Antimicrobial Activity of 2‐Methyl‐5‐nitroaniline Derivatives: A Structure‐Activity Relationship Study

Contact Info

Product

Resources

About

Copper‐Catalyzed Oxidative Dehydrogenative C(sp³)−H Bond Amination of (Cyclo)Alkanes using NH‐Heterocycles as Amine Sources

Copper‐Catalyzed Oxidative Dehydrogenative C(sp³)−H Bond Amination of (Cyclo)Alkanes using NH‐Heterocycles as Amine Sources