Synthesis, biological evaluation, molecular docking, molecular dynamics and DFT studies of quinoline-fluoroproline amide hybrids

Ganesan, M.S.; Raja, K. Kanmani; Murugesan, Sankaranarayanan; Kumar, Banoth Karan; Rajagopal, Gurusamy; Thirunavukkarasu, Sappanimuthu

doi:10.1016/j.molstruc.2020.128360

Cited by 31 publications

(18 citation statements)

References 33 publications

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“…These chemicals share the same glucose ring structure as acarbose (a possible amylase inhibitor). [20][21][22] By generating hydrogen bonds in the acarbose binding catalytic site, these complex ring structures with varied hydroxyl and carbonyl group orientations stabilize the enzyme-inhibitor complex. The protein-ligand combination is stabilized by hydrogen bonds formed by different binding site residues Glu233, Asp300, and His299.…”

Section: Introductionmentioning

confidence: 99%

Recent Developments in the Synthesis of N‐Heterocyclic Compounds as α‐Amylase Inhibitors via In‐Vitro and In‐Silico Analysis: Future Drugs for Treating Diabetes

et al. 2022

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In nature, N‐heterocyclic compounds and their derivatives are abundant. They serve as the building blocks of many biological entities, such as enzymes, alkaloids, hormones, antibiotics, and vitamins. The treatment of diabetes is one of the major applications of heterocyclic compounds. Natural as well as synthetic, both types of heterocyclic compounds show anti‐diabetic activity. There is a plethora of literature on the hyper/hypoglycaemic activity of natural compounds. This review discusses the synthesis methods, yields of the reactions and Inhibitory concentration (IC50) values of all the synthesized derivatives via different assays such as 3,5‐dinitrosalicylic acid (DNS) or starch assays. IC50 values of all the derivatives have been compared with those of standard acarbose. Structure activity relationship of most potential compounds with α‐amylase enzyme is established to show the type of interactions between them. Molecular docking studies show the type of interaction between compounds and enzyme.

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Section: Introductionmentioning

confidence: 99%

Recent Developments in the Synthesis of N‐Heterocyclic Compounds as α‐Amylase Inhibitors via In‐Vitro and In‐Silico Analysis: Future Drugs for Treating Diabetes

et al. 2022

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“…Sharma et al have reported the synthesis and evaluation of prolyl-Fluropyrrolidine derivatives as DPP-4 inhibitors. [53] The synthetic steps involved the BOC protection of L-Proline (64) followed by amide formation with 3-fluoropyrrolidine 66 to give (67). Next step involved the BOC deprotection to afford (68) Liu et al have reported the design, synthesis and biological evaluation of (S)-phenylalanine and alanine derivatives with a 2-cyanopyrrolidine moiety as potent DPP-IV inhibitors.…”

Section: Chemistryselectmentioning

confidence: 99%

“…Ganesan et al have reported the synthesis and α-amylase inhibitory activity of quinoline-fluroproline amide hybrids. [67] The first step of the synthesis involved the conversion of 4-cis fluroproline 161 into its corresponding methyl ester In one more successful attempt, Ganesan et al designed the synthesis of novel quinoline bearing proline derivatives for their effect on α-amylase activity. [68] The first step of the synthesis involved the conversion of proline derivative 166 to ChemistrySelect respectively).…”

Section: Chemistryselectmentioning

confidence: 99%

Pyrrolidine Derivatives as Anti‐diabetic Agents: Current Status and Future Prospects

Bhat

Tandon

2022

ChemistrySelect

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Diabetes Mellitus (DM) is one of the leading causes of deaths worldwide and is becoming an epidemic in many countries. Sedentary lifestyles, less physical activity, environmental and genetic changes are some of the factors which are responsible for the disease. It is putting a lot of economic burden especially on developing and under developed countries. Hence there is a dire need for the management of this disease. The use of current available therapies is associated with one or more side effects or financial burden. From the past few years, pyrrolidine derivatives have grabbed much of the attention of the researchers for the development of the novel molecules that can be used as a drug candidate for the treatment of Diabetes Mellitus. The current review attempts and aims at compiling the important work done in this relevant area which will help the researchers to design and synthesize the novel Pyrrolidine derivatives as antidiabetic agents with desired clinical outputs.

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“…Minimalisasi energi dapat mempermudah dan menyetabilkan susunan ikatan selama penambatan molekul, penambahan hidrogen, dan konversi struktur dua dimensi menjadi tiga dimensi [9]. Minimisasi energi dengan medan gaya (force field) seperti medan gaya mekanika molekular (molecular-mechanics force fields, MMFF94) juga diketahui dapat digunakan untuk menghitung energi potensial dan parameter lainnya seperti regangan ikatan, sudut lekukan, panjang lekukan, gaya torsi, lekukan out-of-plane, interaksi van der Waals, dan elektrostatik [8].…”

Section: Pendahuluanunclassified

“…Minimisasi energi dengan Open Babel PyRx menghasilkan ligan 1b dan L-1MTb dengan nilai energi minimisasi (EM) yang lebih rendah. Minimisasi energi yang menggambarkan kestabilan konformasi struktur molekul berdasarkan nilai EM [9] menginformasikan bahwa algoritma conjugate gradient Open Babel dalam PyRx menghasilkan regangan ikatan (bondstretching), sudut lekukan (bending), panjang lekukan, gaya torsinal (torsion force), lekukan out-of-plane, interaksi van der Waals, dan elektrostatik yang lebih baik untuk kestabilan senyawa 1 dan L-1MT [14,15]. Algoritma conjugate gradient Open Babel diketahui merupakan algoritma umum yang digunakan untuk menyelesaikan sistem persamaan linier berdasarkan penemuan titik minimum dari suatu fungsi kuadrat [16].…”

Section: Preparasi Ligan Dan Makromolekul 2d0tunclassified

Pengaruh Minimisasi Energi MMFF94 dengan MarvinSketch dan Open Babel PyRx pada Penambatan Molekular Turunan Oksindola Tersubstitusi

Hanif¹,

Lukis²,

Fadlan³

2020

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In silico technique is widely used for drug discovery because it can predict the conformation of ligands in protein macromolecules and it can calculate the binding affinity. The energy minimization is carried out to make the ligand more stable near the initial state during molecular docking process. The Merck Molecular Force Field (MMFF94) is one type of energy minimization process often used in organic compounds. The molecular docking of substituted oxindole derivatives on indoleamine macromolecules 2,3-dioxygenase (IDO-1, PDB: 2D0T) by MMFF94 minimization operated by MarvinSketch and Open Babel in PyRx showed different results. The binding affinity energy obtained was also quite different, but the ligands have the same conformation and bind the same residue with slightly different bond distances. Keywords: Molecular docking, energy minimization, substituted oxindole, Merck Molecular Force Field 94 Teknik in silico banyak digunakan untuk penemuan senyawa obat karena dapat memprediksi konformasi suatu ligan dalam makromolekul protein dan mampu menghitung nilai afinitas ikatan. Proses minimisasi energi dilakukan untuk menjadikan ligan lebih stabil mendekati keadaan awal selama penambatan molekular berlangsung. Merck Molecular Force Field (MMFF94) adalah salah satu jenis persamaan minimisasi energi yang sering digunakan pada senyawa organik. Hasil pengujian pengaruh minimisasi energi dengan MMFF94 menggunakan program MarvinSketch dan Open Babel dalam PyRx pada turunan oksindola tersubstitusi alkil terhadap makromolekul 2,3-dioxygenase indoleamine (IDO-1, PDB: 2D0T) menunjukkan hasil dengan nilai yang berbeda. Energi afinitas ikatan yang didapatkan juga cukup berbeda, namun ligan memiliki konformasi yang sama dan mengikat residu yang sama dengan jarak ikatan yang sedikit berbeda. Kata kunci: Penambatan molekular, minimisasi energi, oksindola tersubstitusi, Merck Molecular Force Field 94

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Synthesis, biological evaluation, molecular docking, molecular dynamics and DFT studies of quinoline-fluoroproline amide hybrids

Cited by 31 publications

References 33 publications

Recent Developments in the Synthesis of N‐Heterocyclic Compounds as α‐Amylase Inhibitors via In‐Vitro and In‐Silico Analysis: Future Drugs for Treating Diabetes

Recent Developments in the Synthesis of N‐Heterocyclic Compounds as α‐Amylase Inhibitors via In‐Vitro and In‐Silico Analysis: Future Drugs for Treating Diabetes

Pyrrolidine Derivatives as Anti‐diabetic Agents: Current Status and Future Prospects

Pengaruh Minimisasi Energi MMFF94 dengan MarvinSketch dan Open Babel PyRx pada Penambatan Molekular Turunan Oksindola Tersubstitusi

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