16778-84-0Relevant articles and documents
A facile synthesis of substituted N-benzoylthiourea
Xu, Xiaoyong,Zhongli,Yang, Zhengyu,Chen, Gang,Qian, Xuhong
, p. 2585 - 2592 (2003)
One pot reaction of benzoyl isothiocyanate and Tris(hydroxymethyl)aminomethane (Tris) at room temperature with polyethylene glycol-400 (PEG-400) as solid-liquid phase-transfer catalyst produced substituted N-benzoylthioureas with high yield. A reasonable pathway for their formation has been suggested.
Theoretical and experimental verification of molecular properties of novel benzamide derivatives using computational platforms and in vitro antibacterial activity
Wanjari, Poonam M.,Mokale, Santosh N.,Bharati, Avinash V.,Ingle, Vishwas N.
, p. 655 - 663 (2021)
A series of N-(benzo[d]oxazol-2-ylcarbamothioyl)-2/4-substituted benzamides were synthesized by the reaction of 2-aminobenzoxazole with apposite benzoyl isothiocyanate. The structure of the newly synthesized compounds was confirmed by chemical tests, elemental (C, H, N, and S), and spectral (IR, 1H NMR, 13C NMR, and mass) analysis. All the synthesized compounds were evaluated experimentally for their antibacterial activity against Gram-positive and Gram-negative bacteria. The test results show moderate to potent antibacterial activity compared to the standard drug. The binding interactions of newly synthesized ligand and protein were correlated using a molecular docking study using a binding pocket of GlcN-6-P synthase. [Figure not available: see fulltext.].
Synthesis and enzyme inhibitory kinetics of some novel 3-(substituted benzoyl)-2-thioxoimidazolidin-4-one derivatives as α-glucosidase/α-amylase inhibitors
Qamar, Rabia,Saeed, Aamer,Saeed, Maria,Shah, Babar Hussain,Ashraf, Zaman,Abbas, Qamar,Seo, Sung Yum
, p. 1528 - 1537 (2018)
The present work describes an efficient and convenient synthesis of a library of novel 3-(substituted benzoyl)-2-thioxoimidazolidin-4-ones (3a–j). The benzoyl isothiocyanates were treated with glycine in the presence of pyridine, the reactants got consumed giving a variety of thioxoimidazolidin-4-ones derivatives under mild reaction conditions. The structures of the compounds were determined by elemental analysis, FTIR, 1H, 13C NMR and mass spectral data. The title compounds were tested for their potential to inhibit the activity of enzymes α-glucosidase and α-amylase. It was found that most of the derivatives showed good enzyme inhibitory activity while compound 3j exhibited excellent activity with IC50 values 0.051 and 0.0082 mM for α-glucosidase and α-amylase, respectively. The presence of 3,5-di-NO2 functional groups at aromatic ring in compound 3j play important role in enzyme inhibitory activity. The enzyme inhibitory kinetic analysis of the most potent derivative 3j revealed that it is a mixed type inhibitor of α-glucosidase with Ki and Ki? values 0.0339 and 0.1562 mM, respectively. It was further investigated that compound 3j formed reversible enzyme inhibitor complex with α-glucosidase. The cytotoxicity of all the synthesized compounds was also evaluated and results showed that none of these compounds displayed toxicity against brine shrimps. Based upon results, it is suggested that compound 3j may act as a lead structure for the development of most potent α-glucosidase inhibitors.
Synthesis of sulfadiazinyl acyl/aryl thiourea derivatives as calf intestinal alkaline phosphatase inhibitors, pharmacokinetic properties, lead optimization, Lineweaver-Burk plot evaluation and binding analysis
Sajid-ur-Rehman,Saeed, Aamer,Saddique, Gufran,Ali Channar, Pervaiz,Ali Larik, Fayaz,Abbas, Qamar,Hassan, Mubashir,Raza, Hussain,Fattah, Tanzeela Abdul,Seo, Sung-Yum
, p. 3707 - 3715 (2018)
To seek the new medicinal potential of sulfadiazine drug, the free amino group of sulfadiazine was exploited to obtain acyl/aryl thioureas using simple and straightforward protocol. Acyl/aryl thioureas are well recognized bioactive pharmacophore containin
Aroylthiourea derivatives of ciprofloxacin drug as DNA binder: Theoretical, spectroscopic and electrochemical studies along with cytotoxicity assessment
Farooqi, Shahid Iqbal,Arshad, Nasima,Perveen, Fouzia,Channar, Pervaiz Ali,Saeed, Aamer,Javeed, Aneela
, p. 83 - 98 (2019)
Aroylthiourea derivatives of ciprofloxacin drug — [1-cyclopropyl-6-fluoro-7-(4-((4-methoxybenzoyl)carbamothioyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid] ATU-1, [1-cyclopropyl-7-(4-((2,4-dibromobenzoyl)carbamothioyl)piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid] ATU-2, and [1-cyclopropyl-7-(4-((3,5-dinitrobenzoyl)carbamothioyl)piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid] ATU-3 were synthesized, characterized and investigated for DNA binding at stomach pH (4.7) and at 37 °C. All findings by using DFT, molecular docking, spectroscopic (UV-, fluorescence; FL-), cyclic voltammetric (CV) and viscometric techniques revealed that these compounds have the potency to bind with DNA via a mixed mode of interaction. The binding affinity of ATU-1 was evaluated comparatively greater with Kb × 104/M?1 (docking; 5.55, UV-; 7.93, FL-; 5.62, CV; 6.06), ΔG/kJmol?1(docking; ?27.07, UV-; ?29.07, FL-; ?28.18, CV; ?28.38) and n (FL-; 1.20, CV; 2.72). Stern-Volmer quenching constant (Ksv) further pointed towards comparatively greater binding affinity of ATU-1 for DNA, while bimolecular quenching constant (Kq) values showed the involvement of static quenching mechanism in the compound — DNA interaction. Comparatively lesser IC50 (7.1 μM) value obtained from biological work on Huh-7 cancer cell line further confirmed the greater anticancer potential of ATU-1 than that of ATU-2&3.
Synthesis, antimycobacterial activity, and acid dissociation constants of polyfunctionalized 3-[2-(pyrrolidin-1-yl)thiazole-5-carbonyl]-2H-chromen-2-one derivatives
Nural, Yahya
, p. 1905 - 1918 (2018)
Abstract: This study reports on synthesis and determination of antimycobacterial activity and acid dissociation constants of polyfunctionalized 3-[2-(pyrrolidin-1-yl)thiazole-5-carbonyl]-2H-chromen-2-one derivatives, containing thiazole, coumarin, and pyrrolidine octahydropyrrolo[3,4-c]pyrrole moieties. The products were synthesized by a cyclization reaction of 5,5-diphenylpyrrolidine N-aroylthioureas or methyl 5-substituted 4,6-dioxo-3,3-diphenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate N-aroylthioureas and 3-(bromoacetyl)coumarin with good to excellent yield (81–97%). The compounds exhibited antimycobacterial activity against the M. tuberculosis H37Rv strain with minimum inhibitory concentration values in the range of 31.25–125?μg/cm3. Acid dissociation constants of the compounds were determined using data which were obtained using a potentiometric titration method in 50% (v/v) dimethyl sulfoxide–water hydroorganic solvent at 25 ± 0.1?°C, at an ionic background of 0.1?mol/dm3 of NaCl. Acid dissociation constants were calculated using the HYPERQUAD computer program. The acid dissociation constants obtained might be associated with SH, OH, and two NH groups, which were formed by the protonation of thiazole and pyrrolidine rings. Graphical abstract: [Figure not available: see fulltext.].
Synthesis, computational studies and enzyme inhibitory kinetics of benzothiazole-linked thioureas as mushroom tyrosinase inhibitors
Ujan, Rabail,Saeed, Aamer,Ashraf, Saba,Channar, Pervaiz Ali,Abbas, Qamar,Rind, Mahboob Ali,Hassan, Mubashir,Raza, Hussain,Seo, Sung-Yum,El-Seedi, Hesham R.
, p. 7035 - 7043 (2020/08/12)
Herein, we report synthesis of a set of benzothiazole-thiourea hybrids with aromatic and aliphatic side chains (BT1 to BT9) using an elegant synthetic strategy. The newly synthesized benzothiazole-thiourea conjugates were subjected to In-vitro tyrosinase inhibition and free radical scavenging activity. Majority of the compounds indicated inhibition considerably improved than the standard; compound (Kojic acid with IC50 = 16.8320 ± 1.1600 μM) BT2 with IC50 = 1.3431 ± 0.0254 μM was found to be the best inhibitor. A non-competitive mode of inhibition of BT2 was disclosed with Ki value of 2.8 μM. In order to study enzyme-inhibitor interactions SAR analysis molecular docking was carried out. The amino groups of thiourea were involved in hydrogen bonding with Glu322 showing the bond length of 1.74 and 2.70 ?, respectively. Moreover, the coupling of π-π was displayed between benzothiazole and benzene rings of His244 and His263, respectively. The outcome of this study might help to develop new inhibitors of melanogenesis, important for cosmetic and food products. Communicated by Ramaswamy H. Sarma.
