63586-34-5

Upstream product

• 628-30-8 n-Propyl isothiocyanate 
• 118-92-3 anthranilic acid 
• 20297-19-2 3-n-propyl-2,4-dioxo-1,3-dihydroquinazoline 
• 107-10-8 propylamine 
• 75-15-0 carbon disulfide 
• 118-48-9 isatoic anhydride 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 333-20-0 potassium thioacyanate 
• 37601-33-5 N-(propyl)-S-methyldithiocarbamic acid 
• 134-20-3 2-carbomethoxyaniline 
• 56814-10-9 2-amino-N-propylbenzamide 
• 2314-48-9 (S,S)-dimethyl trithiocarbonate 

Downstream Products

• 852308-02-2 C₁₉H₁₈N₂O₂S 
• 1371942-98-1 C₂₀H₂₀N₂O₂S 
• 939142-17-3 C₁₉H₁₇ClN₂O₂S 
• 880410-57-1 C₁₉H₁₇BrN₂O₂S 

Relevant academic research and scientific papers

Synthesis and Pharmacological Evaluation of 3-propyl-2-substitutedamino-3H-quinazolin-4-ones as Analgesic and Anti-Inflammatory Agents

A variety of novel 3-propyl-2-substitutedamino-quinazolin-4(3H)-ones were synthesized by reacting the amino group of 2-hydrazino-3-propyl quinazolin-4(3H)-one with a variety of aldehydes and ketones. The starting material 2-hydrazino-3-propyl quinazolin-4(3H)-one was synthesized from propylamine. The title compounds were investigated for analgesic and anti-inflammatory activities. The compound 2-(1-ethylpropylidene-hydrazino)-3-propyl-quinazolin-4(3H)-one (SR2) emerged as the most active compound of the series, and it is more potent in its analgesic and anti-inflammatory activities when compared with the reference standard diclofenac sodium.

Design, synthesis, biological evaluation, and molecular docking study of thioxo-2,3-dihydroquinazolinone derivative as tyrosinase inhibitors

Tyrosinase is known to be a key enzyme in melanogenesis and hyperpigmentation. In this study, a series of thioxo-dihydroquinazolinone compounds were designed and synthesized as tyrosinase inhibitors. Among the investigated compounds, 4m demonstrated the best inhibitory activity with an IC50 value of 15.48 μM compared to kojic acid as a positive control with IC50 value of 9.30 μM. In kinetic evaluation against tyrosinase, 4m depicted a mixed inhibition pattern. Additionally, antioxidant evaluations exhibited moderate to weak potency in 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. The detailed interactions and binding mode toward tyrosinase of the most potent derivative were explicated by molecular docking study. Moreover, the computer-aided drug-likeness and pharmacokinetic studies were also carried out.

The natural-based optimization of kojic acid conjugated to different thio-quinazolinones as potential anti-melanogenesis agents with tyrosinase inhibitory activity

Melanin pigment and melanogenesis are a two-edged sword. Melanin has a radioprotection role while melanogenesis has undesirable effects. Targeting the melanogenesis pathway, a series of kojyl thioether conjugated to different quinazolinone derivatives were designed, synthesized, and evaluated for their inhibitory activity against mushroom tyrosinase. All the synthesized compounds were screened for their anti-tyrosinase activity and all derivatives displayed better potency than kojic acid as the positive control. In this regard, 5j and 5h as the most active compounds showed an IC50 value of 0.46 and 0.50 μM, respectively. In kinetic evaluation against tyrosinase, 5j depicted an uncompetitive inhibition pattern. Designed compounds also exhibited mild antioxidant capacity. Moreover, 5j and 5h achieved good potency against the B16F10 cell line to reduce the melanin content, whilst showing limited toxicity against malignant cells. The proposed binding mode of new inhibitors evaluated through molecular docking was consistent with the results of structure–activity relationship analysis.

Design, synthesis, in vitro and in silico biological assays of new quinazolinone-2-thio-metronidazole derivatives

A new series of quinazolinone-2-thio-metronidazole derivatives 9a-o was designed, synthesized and assayed for their activities against metabolic enzymes human carbonic anhydrase I and II (hCAs I and II), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glucosidase. The results indicated that all the synthesized compounds exhibited excellent inhibitory activities against mentioned enzymes as compared with standard inhibitors. Representatively, the most potent compound against CA enzymes, 4-fluorophenyl derivative 9i, was 4 and 7-times more potent than standard inhibitor acetazolamide against hCA I and II, respectively; 4-fluorobenzyl derivative 9m as the most potent compound against cholinesterase enzymes, was around 11 and 21-times more potent than standard inhibitor tacrine against AChE and BChE, respectively; the most active α-glucosidase inhibitor 9h with 4-methoxyphenyl moiety was 5-times more active that acarbose as standard inhibitor. Furthermore, in order to study interaction modes of the most potent compounds in the active site of their related enzymes, molecular modeling was performed. Druglikeness, ADME, and toxicity profile of the compounds 9i, 9m, and 9h were also predicted.

Identification of a New Heterocyclic Scaffold for Inhibitors of the Polo-Box Domain of Polo-like Kinase 1

As a mitotic-specific target widely deregulated in various human cancers, polo-like kinase 1 (Plk1) has been extensively explored for anticancer activity and drug discovery. Although multiple catalytic domain inhibitors were tested in preclinical and clinical studies, their efficacies are limited by dose-limiting cytotoxicity, mainly from off-target cross reactivity. The C-terminal noncatalytic polo-box domain (PBD) of Plk1 has emerged as an attractive target for generating new protein-protein interaction inhibitors. Here, we identified a 1-thioxo-2,4-dihydro-[1,2,4]triazolo[4,3-a]quinazolin-5(1H)-one scaffold that efficiently inhibits Plk1 PBD but not its related Plk2 and Plk3 PBDs. Structure-activity relationship studies led to multiple inhibitors having ≥10-fold higher inhibitory activity than the previously characterized Plk1 PBD-specific phosphopeptide, PLHSpT (Kd ～450 nM). In addition, S-methyl prodrugs effectively inhibited mitotic progression and cell proliferation and their metabolic stability was determined. These data describe a novel class of small-molecule inhibitors that offer a promising avenue for future drug discovery against Plk1-addicted cancers.

Novel quinazolin–sulfonamid derivatives: synthesis, characterization, biological evaluation, and molecular docking studies

In the design of novel drugs, the formation of hybrid molecules via the combination of several pharmacophores can give rise to compounds with interesting biochemical profiles. A series of novel quinazolin–sulfonamid derivatives (9a–m) were synthesized, characterized and evaluated for their in vitro antidiabetic, anticholinergics, and antiepileptic activity. These synthesized novel quinazolin–sulfonamid derivatives (9a–m) were found to be effective inhibitor molecules for the α-glycosidase, human carbonic anhydrase I and II (hCA I and hCA II), butyrylcholinesterase (BChE) and acetylcholinesterase (AChE) enzyme, with Ki values in the range of 100.62 ± 13.68–327.94 ± 58.21 nM for α-glycosidase, 1.03 ± 0.11–14.87 ± 2.63 nM for hCA I, 1.83 ± 0.24–15.86 ± 2.57 nM for hCA II, 30.12 ± 3.81–102.16 ± 13.87 nM for BChE, and 26.16 ± 3.63–88.52 ± 20.11 nM for AChE, respectively. In the last step, molecular docking calculations were made to compare biological activities of molecules against enzymes which are achethylcholinesterase, butyrylcholinesterase and α-glycosidase. Communicated by Ramaswamy H. Sarma.

CuBr-catalysed one-pot multicomponent synthesis of 3-substituted 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives

A novel methodology is presented for the synthesis of 3-substituted 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives based on an efficient tandem multicomponent reaction using copper bromide as catalyst. This methodology is based on the multicomponent one-pot reaction of methyl 2-bromobenzoate, phenylisothiocyanate derivatives and sodium azide in the presence of copper bromide and l-proline under basic conditions. To show the generality of the method, various phenylisothiocyanates bearing electron-donating or electron-withdrawing functionalities were used and the desired products were obtained in high isolated yields.

A green and efficient synthesis of 2-thioxoquinazolinone derivatives in water using potassium thiocyanate

Green chemistry is one of the most important routes for the synthesis of heterocyclic compounds. In this regard, the synthesis of 2-thioxoquinazolinone derivatives was achieved by condensation of versatile materials including isatoic anhydride, amine and potassium thiocyanate in the green medium of water. This convenient and ef?cient method affords the desired products with good to excellent yields.

Design, synthesis and anticonvulsant activity of some newer 3H-quinazolin-4-one derivatives

In the present investigation, a series of 2-[2-(aryl)-2-oxo-ethylsulfanyl]- 3-(aryl/propyl)-3H-quinazolin-4-ones have been synthesized and tested for their potential against seizures in mice. All the newly synthesized compounds show moderate to high protection against 6 Hz partial seizure with compound 2b, 2-(2-oxo-2-p-tolyl-ethylsulfanyl)-3-phenyl-3H-quinazolin-4-one emerging as the most active anticonvulsant agent endowed with neuroprotective effect against NMDA and kainate induced excitotoxicity. The results of whole brain GABA assay indicates that the seizure protective activity of 2b can be either due to the increased brain GABA level or due to neuroprotective action.

Convenient and sequential one-pot route for synthesis of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives

A new and efficient synthetic process has been developed for preparation of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives. The related products were synthesized through reaction of isatoic anhydride, amines/anthranilic acids, and carbon disulfide (CS2) in the presence of potassium hydroxide in ethanol at reflux. Graphical abstract: [Figure not available: see fulltext.]