Synthesis of biphenyl derivatives as ACE and α-amylase inhibitors

Meti, Gangadhar Y.; Kamble, Ravindra R.; Biradar, Dharesh B; Margankop, Sheetal B.

doi:10.1007/s00044-013-0574-8

Cited by 7 publications

(6 citation statements)

References 25 publications

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“…Compound MP-416 can be obtained in two synthetic steps ( Figure 16 ). First, an alkylation reaction of naphthalene V with carboxylic acid VI using potassium carbonate (K 2 CO 3 ) as a base in acetone will provide intermediate VII [ 55 ]. Finally, the desired carboxamide MP-416 will be provided by the reaction between carboxylic acid VII and amine VIII using hydroxybenzotriazole (HOBT), N,N-diisopropylethylamine (DIPEA) as a base, 2-(1H-benzotriazol-1-yl)-1,1,3,3 tetramethyluronium hexafluorophosphate (HBTU) as a coupling agent and dichloromethane (DCM) as solvent [ 56 ].…”

Section: Resultsmentioning

confidence: 99%

Identification of Potential New Aedes aegypti Juvenile Hormone Inhibitors from N-Acyl Piperidine Derivatives: A Bioinformatics Approach

Lima

Bastos

Ferreira

et al. 2022

IJMS

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Aedes aegypti mosquitoes transmit several human pathogens that cause millions of deaths worldwide, mainly in Latin America. The indiscriminate use of insecticides has resulted in the development of species resistance to some such compounds. Piperidine, a natural alkaloid isolated from Piper nigrum, has been used as a hit compound due to its larvicidal activity against Aedes aegypti. In the present study, piperidine derivatives were studied through in silico methods: pharmacophoric evaluation (PharmaGist), pharmacophoric virtual screening (Pharmit), ADME/Tox prediction (Preadmet/Derek 10.0®), docking calculations (AutoDock 4.2) and molecular dynamics (MD) simulation on GROMACS-5.1.4. MP-416 and MP-073 molecules exhibiting ΔG binding (MMPBSA −265.95 ± 1.32 kJ/mol and −124.412 ± 1.08 kJ/mol, respectively) and comparable to holo (ΔG binding = −216.21 ± 0.97) and pyriproxyfen (a well-known larvicidal, ΔG binding= −435.95 ± 2.06 kJ/mol). Considering future in vivo assays, we elaborated the theoretical synthetic route and made predictions of the synthetic accessibility (SA) (SwissADME), lipophilicity and water solubility (SwissADME) of the promising compounds identified in the present study. Our in silico results show that MP-416 and MP-073 molecules could be potent insecticides against the Aedes aegypti mosquitoes.

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Section: Resultsmentioning

confidence: 99%

Identification of Potential New Aedes aegypti Juvenile Hormone Inhibitors from N-Acyl Piperidine Derivatives: A Bioinformatics Approach

Lima

Bastos

Ferreira

et al. 2022

IJMS

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“…The intermediates (4,17,36,45), 19 (71-77, 81, 83, 84, 92, 94), 20,21,23 (70, 78, 79) 20,21 (93, 95) 20,22 (80, 82, 86, 87) 20,23,25 (85, 88, 90, 91) 20,24,26 (92) 20,27 were synthesized as per earlier reported procedures while compounds (5-9, 18-23, 30-32, 37, 39-41, 46-49, 54-60, 68, 69) were obtained from commercial sources. HCl (pH 5.5-6.0).…”

Section: General Methodsmentioning

confidence: 99%

“…Found: C,64.51;H,6.03;N,)methylamino]phenyl}-1H-tetrazole (27). Following method B 5-(4-aminophenyl)-1H-tetrazole (21) (0.39 g, 2.6 mM) afforded compound (27) (0.32 g, 44%), mp ¼ 90-92 C. IR (KBr): 3359, 3134, 2962, 1665, 1611, 1502, 1465, 1400, 1271, 1208, 1174, ,5.79;N,22.51. Found: C,60.46;H,5.61;N,)methylamino]phenyl}-1H-tetrazole (28).…”

Section: General Methodsmentioning

confidence: 99%

“…3-Butylquinazolinones of types (B and C) were prepared as per Scheme 2. The required 2-chloromethyl derivative 19 (17) was reacted with the respective anilines (18)(19)(20)(21)(22)(23) to obtain the anilinomethyl derivatives (24)(25)(26)(27)(28)(29). In another reaction, the 2-chloromethyl derivative 19 (17) was reacted with N-substituted piperazines (30)(31)(32) to obtain the desired piperazinomethyl derivatives (33)(34)(35).…”

Section: Chemistrymentioning

confidence: 99%

“…In these compounds the aryl moiety (Z) was directly linked to the piperazine ring. [20][21][22][23][24][25][26][27] So, it was envisaged to introduce one/two carbon spacer between the piperazine ring and the aryl moiety, and observe the impact of this change on the a 1 /AT 1 dual antagonistic activity. The spacer Scheme 2 Synthesis of compounds (24-29 and 33-35); (d): anh.…”

Section: Chemistrymentioning

confidence: 99%

See 2 more Smart Citations

Exploration of 6,7-dimethoxyquinazoline derivatives as dual acting α₁- and AT₁-receptor antagonists: synthesis, evaluation, pharmacophore & 3D-QSAR modeling and receptor docking studies

et al. 2016

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Design, Synthesis and Antidiabetic Activity of Biphenylcarbonitrile‐Thiazolidinedione Conjugates as Potential α‐Amylase Inhibitors

et al. 2021

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The α‐amylase inhibition has been considered as an effective therapeutic approach against chronic Type 2 Diabetes mellitus (DM). In the present study, a series of biphenylcarbonitrile‐thiazolidinedione conjugates have been synthesized and evaluated for their antidiabetic activity viaα‐amylase inhibition. It was found that most of the conjugates (14 a–j) exhibited significant α‐amylase inhibition activity compared to the standard drug Acarbose. Off these, compound 14 b,14 c and 14 dwere most potent with IC50 value 0.13 μM, 0.15 μM and0.13 μM respectively. To ascertain ligand‐receptor interactions, the in silico molecular docking studies of these conjugates (14 a–j) have been carried out into the Acarbose active site of barley (malt) α‐amylase enzyme. The results have shown fair corroboration between significant α‐amylase inhibition activity of 14 b, 14 c and 14 d and their docking scores compared to the standard drug Acarbose. This study demonstrated that biphenylcarbonitrile‐thiazolidinedione conjugate could be a plausible pharmacophore for targeting α‐amylase for the treatment of Type 2 Diabetes mellitus.

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Synthesis of biphenyl derivatives as ACE and α-amylase inhibitors

Cited by 7 publications

References 25 publications

Identification of Potential New Aedes aegypti Juvenile Hormone Inhibitors from N-Acyl Piperidine Derivatives: A Bioinformatics Approach

Identification of Potential New Aedes aegypti Juvenile Hormone Inhibitors from N-Acyl Piperidine Derivatives: A Bioinformatics Approach

Exploration of 6,7-dimethoxyquinazoline derivatives as dual acting α₁- and AT₁-receptor antagonists: synthesis, evaluation, pharmacophore & 3D-QSAR modeling and receptor docking studies

Design, Synthesis and Antidiabetic Activity of Biphenylcarbonitrile‐Thiazolidinedione Conjugates as Potential α‐Amylase Inhibitors

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Synthesis of biphenyl derivatives as ACE and α-amylase inhibitors

Cited by 7 publications

References 25 publications

Identification of Potential New Aedes aegypti Juvenile Hormone Inhibitors from N-Acyl Piperidine Derivatives: A Bioinformatics Approach

Identification of Potential New Aedes aegypti Juvenile Hormone Inhibitors from N-Acyl Piperidine Derivatives: A Bioinformatics Approach

Exploration of 6,7-dimethoxyquinazoline derivatives as dual acting α1- and AT1-receptor antagonists: synthesis, evaluation, pharmacophore & 3D-QSAR modeling and receptor docking studies

Design, Synthesis and Antidiabetic Activity of Biphenylcarbonitrile‐Thiazolidinedione Conjugates as Potential α‐Amylase Inhibitors

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Exploration of 6,7-dimethoxyquinazoline derivatives as dual acting α₁- and AT₁-receptor antagonists: synthesis, evaluation, pharmacophore & 3D-QSAR modeling and receptor docking studies