73945-65-0Relevant academic research and scientific papers
Design, Synthesis, and Insecticidal Activity of Novel Doramectin Derivatives Containing Acylurea and Acylthiourea Based on Hydrogen Bonding
Bai, Ping,Cheng, Yao,Lu, Xiaoxia,Yang, Jian,Zhang, Qi,Zheng, Cheng
, p. 5806 - 5815 (2020/06/19)
Our recent investigation on the insecticidal activities of several doramectin derivatives preliminarily revealed that the presence of hydrogen bonds at the C4″ position of the molecule with target protein γ-aminobutyric acid (GABA) receptor was crucial for retaining high insecticidal activity. As a continuation of our research work on the development of new insecticides, two series of novel acylurea and acylthiourea doramectin derivatives were designed and synthesized. The bioassay results indicated that the newly synthesized compounds (5o, 5t, and 6t) exhibited higher insecticidal activity against diamondback moth, oriental armyworm, and corn borer than the control compounds doramectin, commercial avermectins, chlorbenzuron, and lead compound 3g in our laboratory. Specifically, compound 5t was identified as the most promising insecticide against diamondback moth, with a final mortality rate of 80.00% at the low concentration of 12.50 mg/L, showing approximately 7.75-fold higher potency than the parent doramectin (LC50 value of 48.1547 mg/L), 6.52-fold higher potency than commercial avermectins (LC50 value of 40.5507 mg/L), and 3.98-fold higher potency than compound 3g (LC50 value of 24.7742 mg/L). Additionally, molecular docking simulations revealed that compound 5t (2.17, 2.20, 2.56, and 2.83 ?) displayed stronger hydrogen-bond action in binding with the GABA receptor, better than that of compound 5o (1.64 and 2.15 ?) and compound 6t (2.20 and 2.31 ?) at the C4″ position. This work demonstrated that these compounds containing hydrogen-bond groups might contribute to the improvement of insecticidal activity and supply certain hints toward structure optimization design for the development of new insecticides.
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 (2018/04/02)
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, carbonic anhydrase inhibitory activity and antioxidant activity of some 1,3-oxazine derivatives
Qamar, Rabia,Saeed, Aamer,Saeed, Maria,Ashraf, Zaman,Abbas, Qamar,Hassan, Mubashir,Albericio, Fernando
, p. 352 - 361 (2018/10/20)
(Table presented.). A series of 1-(6-methyl-2-substituted phenyl-4-thioxo-4H-1,3-oxazin-5-yl)ethanones (3a-n) were synthesized by the reaction of benzoyl isothiocyanates with active methylene compound acetylacetone in the presence of triethyl amine in a one-pot process. The structures of the products were elucidated by elemental analyses, FT-IR, 1H NMR, 13C NMR, and mass spectroscopy. These new 1,3-oxazine derivatives were evaluated for their inhibitory activity against carbonic anhydrase II. Results for in vitro assay revealed that compound 3b having 4-methoxy phenyl moiety was the most potent inhibitor with IC50 value of 0.144 ± 0.008 μM. It exhibited higher enzyme inhibitory activity as compared to the standard acetazolamide (IC50 = 0.997 ± 0.061 μM). The compounds 3c, 3h, and 3n also displayed superior inhibitory activities compared to the rest of the synthesized oxazine derivatives. The radical scavenging activity of oxazine derivatives was also performed and it was found that compounds showed moderate antioxidant activity. Lipinski rule confirmed the therapeutic potential of the synthesized compounds. Molecular docking studies were also performed to further understand the binding affinity of these compounds with PDBID 1V9E which confirmed that the synthesized derivatives bind in the active binding site of the target protein. Based upon our results, it is proposed that compound 3b may serve as a lead structure to design more potent carbonic anhydrase inhibitors.
Synthesis, spectroscopic investigation, and DFT study of: N, N ′-disubstituted ferrocene-based thiourea complexes as potent anticancer agents
Asghar, Faiza,Fatima, Saira,Rana, Sadaf,Badshah, Amin,Butler, Ian S.,Tahir, Muhammad Nawaz
, p. 1868 - 1878 (2018/02/17)
In the present work, the synthesis, characterization (FT-IR, multinuclear (1H and 13C) NMR, AAS, Raman, and elemental analyses), DNA binding (cyclic voltammetry, UV-Vis spectroscopy), and in vitro biological screening of nine new fer
Biologically active: Halo -substituted ferrocenyl thioureas: Synthesis, spectroscopic characterization, and DFT calculations
Asghar, Faiza,Rana, Sadaf,Fatima, Saira,Badshah, Amin,Lal, Bhajan,Butler, Ian S.
, p. 7154 - 7165 (2018/05/04)
In our search for new therapeutic agents, ferrocene-based thioureas (M1-M9) were successively synthesized and characterized by various analytical techniques like FT-IR, Raman, CHNS, AAS, and multinuclear (1H and 13C) NMR. The interac
Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea against Meloidogyne incognita
Chang, Yaning,Zhang, Jingwei,Chen, Xiulei,Li, Zhong,Xu, Xiaoyong
supporting information, p. 2641 - 2644 (2017/05/10)
Two series of novel 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea were designed and synthesized. The bioassay results showed that most of the test compounds showed good nematicidal activity against M. incognita at the concentration of 10.0?mg?L?1 in vivo. The compounds A13, A17 and B3 showed excellent nematicidal activity on the second stage juveniles of the root-knot nematode with the inhibition rate of 51.3%, 58.3% and 51.3% at the concentration of 1.0?mg?L?1 respectively. It suggested that the structure of 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea could be optimized further.
Straightforward Approach Toward Dihydrothiazoles via Intramolecular Bromocyclization
Sadat-Ebrahimi, Seyed Esmail,Ganjizadeh Zarj, Marzieh,Moghimi, Setareh,Yahya-Meymandi, Azadeh,Mahdavi, Mohammad,Arab, Saman,Shafiee, Abbas,Foroumadi, Alireza
, p. 2142 - 2147 (2015/09/01)
An intramolecular bromonium ion-assisted cyclization with sulfur as an internal nucleophile is described. Starting from benzoyl chlorides, this method provides an easy procedure for the synthesis of dihydrothiazole derivatives in moderate to good yields.
Structure-Activity Relationships and Anti-inflammatory Activities of N-Carbamothioylformamide Analogues as MIF Tautomerase Inhibitors
Zhang, Yu,Xu, Lei,Zhang, Zhiqiang,Zhang, Zhiyu,Zheng, Longtai,Li, Dan,Li, Youyong,Liu, Feng,Yu, Kunqian,Hou, Tingjun,Zhen, Xuechu
, p. 1994 - 2004 (2015/10/06)
Macrophage migration inhibitory factor (MIF), a proinflammatory cytokine, is an attractive therapeutic target for the treatment of inflammatory diseases. In our previous study, 3-[(biphenyl-4-ylcarbonyl)carbamothioyl]amino benzoic acid (compound 1) was discovered as a potent inhibitor of MIF by docking-based virtual screening and bioassays. Here, a series of analogues of compound 1 derived from similarity search and chemical synthesis were evaluated for their MIF tautomerase activities, and their structure-activity relationships were then analyzed. The most potent inhibitor (compound 5) with an IC50 of 370 nM strongly suppressed lipopolysaccharide (LPS)-induced production of TNF-α and IL-6 in a dose-dependent manner and significantly enhanced the survival rate of mice with LPS-induced endotoxic shock from 0 to 35% at 0.5 mg/kg and to 45% at 1 mg/kg, highlighting the therapeutic potential of the MIF tautomerase inhibition in inflammatory diseases.
Synthesis, structure-activity relationships, and anticonvulsant activities of 2-amino-4H-pyrido[3,2-e][1,3]thiazin-4-one derivatives as orally active AMPA receptor antagonists
Inami, Hiroshi,Shishikura, Jun-Ichi,Yasunaga, Tomoyuki,Ohno, Kazushige,Yamashita, Hiroshi,Kato, Kota,Sakamoto, Shuichi
, p. 1788 - 1799 (2015/03/30)
As part of a program aimed at discovering orally active 2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA) receptor antagonists, we screened our compound library and identified 2-[allyl(4-methylphenyl)amino]-4H-pyrido[3,2-e][1,3]thiazin-4-on
Biological evaluation of halogenated thioureas as cholinesterases inhibitors against alzheimer's disease & molecular modeling studies
Iqbal, Jamshed,Zaib, Sumera,Saeed, Aamer,Muddassar, Muhammad
, p. 488 - 494 (2015/06/22)
Acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition is thought to be an encouraging approach towards the therapy of Alzheimer's disease (AD). The current paper targets to give a concise information of mono and dihalo- substituted thioureas similarity with anti-AD potential. The present results represent evaluation of cholinesterase inhibitory potential for halogenated thioureas derivatives. Compound 1t was constituted to be highly potent inhibitor with Ki value 0.12 ± 0.05 μM against AChE, while 1b was most the active inhibitor for BChE with Ki value of 0.03 ± 0.001 μM. Molecular docking simulations were performed using the homology models of both cholinesterases in order to explore the plausible binding modes of synthesized compounds.
