Synthesis, structure, and bioactivity of N′-substituted benzylidene-3,4,5-trimethoxybenzohydrazide and 3-acetyl-2-substituted phenyl-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole derivatives

Jin, Linhong; Jiang, Chen; Song, Baoan; Chen, Zhuo; Yang, Song; Li, Qianzhu; Hu, Deyu; Xu, Ruiqing

doi:10.1016/j.bmcl.2006.07.048

Cited by 111 publications

(38 citation statements)

References 11 publications

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“…The chalcones (3)(4)(5)(6) showed yields in the range of 40-50% due the presence of the bromine atom in the starting material acetophenone, which stabilizes the enolate intermediate of the reaction making it less reactive. This effect was not observed for the chalcones (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20), which showed yields in the range of 70-98%.…”

Section: Physicochemical Data Of the Synthesized Compoundsmentioning

confidence: 85%

“…The solid obtained was filtered and recrystallized from hot methanol to afford the 3,4,5-trimethoxybenzohydrazide (80%). 17 The hydrazides were synthesized as shown in Scheme 2. 3,4,5-trimethoxybenzohydrazide (2 mmol) was mixed with the appropriate aldehyde (2 mmol) in methanol (15 mL) and refluxed for 2 h. After cooling, the crude product was collected by filtration, washed and recrystallized from hot ethanol to give white solids.…”

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confidence: 99%

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Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi

Borchhardt¹,

Mascarello²,

Chiaradia³

et al. 2010

J. Braz. Chem. Soc.

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A doença de Chagas, uma infecção parasitária amplamente distribuída na América Latina, é um problema grave de saúde pública com conseqüências devastadoras em termos de morbidade e mortalidade humana. A enzima cruzaína é a principal cisteíno protease do Trypanosoma cruzi, agente etiológico da tripanossomíase Americana ou doença de Chagas, e foi selecionada como alvo atrativo para o desenvolvimento de novos fármacos tripanocidas. No presente trabalho, a síntese e os efeitos inibitórios de uma série de trinta e três chalconas e sete hidrazidas são descritos contra a enzima cruzaína de T.cruzi. A maioria dos compostos mostraram inibição promissora in vitro (valores de IC 50 na faixa de 20-60 μM), o que sugere o potencial desses compostos como candidatos a líderes para contínuo desenvolvimento. Doze compostos são inéditos, sendo que quatro destes (7, 13, 16 e 18) estão entre os inibidores mais potentes da série.Chagas' disease, a parasitic infection widely distributed throughout Latin America, is a major public health problem with devastating consequences in terms of human morbidity and mortality. The enzyme cruzain is the major cysteine protease from Trypanosoma cruzi, the etiologic agent of American trypanosomiasis or Chagas' disease, and has been selected as an attractive target for the development of novel trypanocidal drugs. In the present work, we describe the synthesis and inhibitory effects of a series of thirty-three chalcone and seven hydrazide derivatives against the enzyme cruzain from T. cruzi. Most of the compounds showed promising in vitro inhibition (IC 50 values in the range of 20-60 μM), which suggest the potential of these compounds as lead candidates for further development. Twelve compounds have not been reported before, and four of them (7, 13, 16 e 18) are among the most potent inhibitors of the series.

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Section: Physicochemical Data Of the Synthesized Compoundsmentioning

confidence: 85%

mentioning

confidence: 99%

Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi

Borchhardt¹,

Mascarello²,

Chiaradia³

et al. 2010

J. Braz. Chem. Soc.

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“…More and more derivatives have been demonstrated to present obvious antimicrobial, antitumor, antifungal activity, etc. [34][35][36][37][38][39][40][41][42] Hence, as part of our agrochemistry program aimed at the search for novel natural product-oriented bioactive molecules, based on the aforementioned, we utilized blactam scaffold as prototype structural unit and planed for the incorporating natural gallic acid and azetidinone moieties in a single molecular scaffold (Fig. 2).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Activity of a Series of Novel N‐Substituted β‐Lactams Derived from Natural Gallic Acid

Cao

Wang

et al. 2011

J Chinese Chemical Soc

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“…The remarkable reactivity of acid hydrazides R-CONHNH 2 [19] and the biological activity associated with their corresponding hydrazones attributed to the presence of the active pharmacophore (-CONH-N=CH-). Hence many hydrazone compounds containing this active moiety are known to exhibit good anticancer bioactivities according to the literature [20]. Some of the Schiff bases complex combinations with metals are used as insecticides, fungicides, herbicides [21].…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis and evaluation of antibacterial activity of 2,2'-(naph- thalene-2,7-diylbis(oxy))bis(N'-substituted acetohydrazide) derivatives

Venkatesan¹,

Satyanarayana²,

Sivakumar³

2012

Bull. Chem. Soc. Eth.

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ABSTRACT. A series of Schiff base of 2,2'-(naphthalene-2,7-diylbis(oxy))bis(N'-substituted acetohydrazide) (4a-m) derivatives has been synthesized by the acid catalyzed condensation of aryl/hetero aromatic aldehydes with 2,2'-(naphthalene-2,7-diylbis(oxy))diacetohydrazide (3) under microwave irradiation and conventional method for comparison. The structures of all the newly synthesized compounds have been characterized by IR, 1 H NMR, 13 C NMR and Mass spectra. All the synthesized compounds have been screened for their in vitro antibacterial activity.

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Synthesis, structure, and bioactivity of N′-substituted benzylidene-3,4,5-trimethoxybenzohydrazide and 3-acetyl-2-substituted phenyl-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole derivatives

Cited by 111 publications

References 11 publications

Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi

Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi

Synthesis and Biological Activity of a Series of Novel N‐Substituted β‐Lactams Derived from Natural Gallic Acid

Microwave-assisted synthesis and evaluation of antibacterial activity of 2,2'-(naph- thalene-2,7-diylbis(oxy))bis(N'-substituted acetohydrazide) derivatives

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