Synthesis, characterization and biological evaluation of fused thiazolo[3,2-a]pyrimidine derivatives

Banothu, Janardhan; Manjulatha, K.; Basavoju, Srinivas; Rajitha, B.; Narra, Muralikrishna; Abbagani, Sadanandam

doi:10.1039/c4ra02514h

Cited by 27 publications

(10 citation statements)

References 32 publications

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“…In light of the above, and as a part of our endeavor in creating a novel heterocyclic hybrids we adopted the hybridization approach,, where a new molecular hybrid was created by amalgamating the four pharmacophores (pyrazole, thiazole, coumarin and benzothiazole motifs) in one molecular framework . We predicted that synergistic effect of these pharmacophores could lead us to a hybrid molecule with the multi‐target mode of action with an expectation of enhanced biological activity.…”

Section: Introductionmentioning

confidence: 99%

“…Some of the biological properties include antioxidant, anticholinesterase activity (AChE and BuChE), [18][19][20] carbonic anhydrase I, II [21,22] and IX inhibiting activities [23] and aflatoxigenic activity. [24] In light of the above, and as a part of our endeavor in creating a novel heterocyclic hybrids [25][26][27] we adopted the hybridization approach, [28,29] where a new molecular hybrid was created by amalgamating the four pharmacophores (pyrazole, thiazole, coumarin and benzothiazole motifs) in one molecular framework. [30] We predicted that synergistic effect of these pharmacophores could lead us to a hybrid molecule with the multi-target mode of action with an expectation of enhanced biological activity.…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis, In Vitro Evaluation and Docking Studies of Pyrazole‐Thiazole Hybrids as Antimicrobial and Antibiofilm Agents

et al. 2018

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In the present study, a series of novel pyrazole‐thiazole hybrids (4a‐l) were designed, synthesized and assessed for their in vitro antimicrobial activity against both Gram‐positive and Gram‐negative pathogenic bacterial and fungal strains. Compounds derived from p‐CH3 phenyl (4b), p‐Br phenyl (4g), 8‐bromocoumarinyl (4k), and 6,8‐dibromocoumarinyl (4l) exhibited promising inhibitory activity against the tested bacterial strains with minimum inhibitory concentration (MIC)/minimum bactericidal concentration (MBC) spectrum of 1.9/7.8 μg/mL to 3.9/7.8 μg/mL. The compounds with p‐CH3 phenyl (4b), p‐OCH3 phenyl (4c), benzo[f]coumarinyl (4j), 8‐bromocoumarinyl (4k) substitutions showed their inhibitory potency against various Candida strains with MIC/minimum fungicidal concentration (MFC) values of 3.9/7.8 μg/mL. Also, anti‐biofilm and toxicity profile of the compounds was also tested. The biofilm inhibition results revealed that the compound 4 j exhibited promising activity with an IC50 value of 11.8 μM against S. aureus MTCC 96, while 4 k showed significant activity against S. aureus MLS16 MTCC 2940, K. planticola MTCC 530 and C. albicans MTCC 3017 with IC50 values of 12, 14 and 16 μM, respectively. The present study has emphasized that thiazole‐pyrazole hybrids with benzothiazole and coumarin scaffolds can be a novel and potent class of molecules with potential biological activities.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, In Vitro Evaluation and Docking Studies of Pyrazole‐Thiazole Hybrids as Antimicrobial and Antibiofilm Agents

et al. 2018

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“…For some of the listed compounds, the presence of HBr molecules in the structure might be quite feasible from a chemical point of view. However, there remained still a total of 13 entries [CSD refcodes BEPQIY (Rů žička et al, 2013), EVAMIX (Cocco et al, 2004), GICSOC (Aureggi et al, 2013), KEKQAS (Wang et al, 1999), KONVEO (Lin et al, 1990), MOMVIV (Surendra Dilip & Gowri, 2014), MOMVIV01 (Gowri et al, 2015), MUFKON (Liang et al, 2002), NAVFOI01 (Zhao et al, 2017), NIJGOC (Liu et al, 1997b), SOCZUH (Banothu et al, 2014), UNESAI (Zhang & Shen, 2011) and YOTSIJ (Monte et al, 1995)], where the simultaneous presence of HBr with a basic moiety (in KEKQAS, HBr and OH À !) is proposed, with H-Br bond lengths ranging from 0.79 to 1.84 Å .…”

Section: Database Surveymentioning

confidence: 99%

HBr or not HBr? That is the question: crystal structure of 6-hydroxy-1,4-diazepane-1,4-diium dibromide redetermined

et al. 2019

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Liu et al. [Chin. J. Struct. Chem. (1996). 15, 371–373] reported the structure of 6-hydroxy-1,4-diazepane di(hydrogen bromide), C5H12N2O·2HBr, which was interpreted in terms of neutral diazepane and HBr molecules. We found, however, ample evidence that the formation of an organic salt, consisting of a diammonium cation and two bromide anions, is more plausible. This interpretation is also in agreement with thermogravimetric analysis and with the observed solution behaviour. The crystal structure of 6-hydroxy-1,4-diazepane-1,4-diium dibromide, C5H14N2O2+·2Br−, measured at 142 K, crystallized in the orthorhombic space group P212121. The structure displays O—H...Br and N—H...Br hydrogen bonding. Contact distances are given. A search in the Cambridge Structural Database for the singly-bonded H—Br moiety revealed a total of 69 structures. The question, whether these structures really include HBr as neutral molecules or rather Br− anions and a protonated substrate such as an amine, is addressed.

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“…Thiazolopyrimidines, whose molecules includes both thiazole and pyrimidine rings, have a structural analogy with the antipsychotic drugs ritanserin and setoperone ( Figure 1) [1][2][3]. To date, a wide spectrum of biological activity of thiazolopyrimidines has been determined: anticancer [4,5], antimicrobial [6,7], anti-inflammatory [8,9], and antiviral [10,11].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3(2)-phosphonylated thiazolo[3,2-a]oxopyrimidines

Kaskevich¹,

Babushkina²,

Gurzhiy³

et al. 2020

Beilstein J. Org. Chem.

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A series of 3(2)-phosphonylated thiazolo[3,2-a]oxopyrimidines was synthesized for the first time by the reactions of chloroethynylphosphonates with unsubstituted and 5(6)-substituted 2-thiouracils. The reaction of chloroethynylphosphonates with 6-substituted 2-thiouracils bearing electron-donor groups (CH3, Ph) proceeded with high regioselectivity involving the cyclization through the N3-nitrogen atom to form new 3-phosphonylated thiazolo[3,2-a]-5-oxopyrimidines with good yield. In the case of unsubstituted and 5-methyl-2-thiouracils, cyclization occurred predominantly through the N1 atom and partially via the N3-nitrogen atom to form a mixture of the corresponding thiazolo[3,2-a]-7- and 5-oxopyrimidines. A dramatic change in the reaction regioselectivity was observed in the case of 6-trifluoromethyl-2-thiouracil that afforded 2- and 3-phosphonylated 5-oxothiazolopyrimidines in a 1:1 ratio.

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Synthesis, characterization and biological evaluation of fused thiazolo[3,2-a]pyrimidine derivatives

Cited by 27 publications

References 32 publications

Design, Synthesis, In Vitro Evaluation and Docking Studies of Pyrazole‐Thiazole Hybrids as Antimicrobial and Antibiofilm Agents

Design, Synthesis, In Vitro Evaluation and Docking Studies of Pyrazole‐Thiazole Hybrids as Antimicrobial and Antibiofilm Agents

HBr or not HBr? That is the question: crystal structure of 6-hydroxy-1,4-diazepane-1,4-diium dibromide redetermined

Synthesis of 3(2)-phosphonylated thiazolo[3,2-a]oxopyrimidines

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