31162-13-7Relevant academic research and scientific papers
One-pot synthesis of triazoloquinazolinones via copper- catalyzed tandem click and intramolecular C-H amidation
Selvaraju, Manikandan,Sun, Chung-Ming
, p. 1329 - 1336 (2014)
A novel and highly efficient copper-catalyzed tandem synthesis of triazoloquinazolinones is explored. The synthetic strategy involves a sequential one-pot click reaction followed by aerobic intramolecular C-H amidation. Two distinct and important transfor
Synthesis, antiproliferative, docking and DFT studies of benzimidazole derivatives as EGFR inhibitors
Alam, Mohammad Mahboob,Alzahrani, Hessah Abdullah,Elhenawy, Ahmed A.,Malebari, Azizah M.,Nazreen, Syed
, (2022/01/04)
In the present work, new benzimidazole linked 1,2,3-triazole hybrids have been synthesized and screened for antiproliferative and EGFR kinase inhibitory activities.The structures of these hybrids were elucidated using IR, NMR, mass spectrometry and elemen
Benzimidazole–galactosides bind selectively to the Galectin-8 N-Terminal domain: Structure-based design and optimisation
Hassan, Mujtaba,van Klaveren, Sjors,H?kansson, Maria,Diehl, Carl,Kova?i?, Rebeka,Baussière, Floriane,Sundin, Anders P.,Dernov?ek, Jaka,Walse, Bj?rn,Zetterberg, Fredrik,Leffler, Hakon,Anderluh, Marko,Toma?i?, Tihomir,Jakopin, ?iga,Nilsson, Ulf J.
, (2021/07/06)
We have obtained the X-ray crystal structure of the galectin-8 N-terminal domain (galectin-8N) with a previously reported quinoline–galactoside ligand at a resolution of 1.6 ?. Based on this X-ray structure, a collection of galactosides derivatised at O3 with triazole, benzimidazole, benzothiazole, and benzoxazole moieties were designed and synthesised. This led to the discovery of a 3-O-(N-methylbenzimidazolylmethyl)–galactoside with a Kd of 1.8 μM for galectin-8N, the most potent selective synthetic galectin-8N ligand to date. Molecular dynamics simulations showed that benzimidazole–galactoside derivatives bind the non-conserved amino acid Gln47, accounting for the higher selectivity for galectin-8N. Galectin-8 is a carbohydrate-binding protein that plays a key role in pathological lymphangiogenesis, modulation of the immune system, and autophagy. Thus, the benzimidazole-derivatised galactosides represent promising compounds for studies of the pathological implications of galectin-8, as well as a starting point for the development of anti-tumour and anti-inflammatory therapeutics targeting galectin-8.
One-Step Synthesis of 2-[(2-Carboxyphenyl)amino]-6-formylnicotinic Acid via Photolysis of 2-Azidobenzoic Acid in the Presence of Weak Bases
Budruev, A. V.,Davydov, D. A.,Dzhons, D. Yu.,Giricheva, M. A.,Pokrovskaia, A. V.
, p. 2013 - 2018 (2021/11/13)
Abstract: 2-Azidobenzoic acid has undergone rearrangement into 2-[(2-carboxyphenyl)amino]-6-formylnicotinic acid under irradiation in aqueous-organic media in the presence of acetates of alkali or alkaline earth metals. The structure of the resulting comp
Design, synthesis, and evaluation of new 4(3H)-quinazolinone derivatives containing a pyrazole carboxamide moiety
Wang, Xiang,Wang, Xiaoyu,Zhou, Banghua,Long, Jiefeng,Li, Pei
, p. 2109 - 2116 (2021/07/10)
A total of 15 new 4(3H)-quinazolinone derivatives containing a pyrazole carboxamide moiety were designed and synthesized in this study. The structures of the target compounds were elucidated using 1H NMR, 13C NMR, MS, and elemental a
Catalyst-Controlled Regioselective Synthesis of Benzotriazlolodiazepin-7-ones and Benzotriazolodiazocin-8-ones
Chen, Kai-Chi,Barve, Indrajeet J.,Sun, Chung-Ming
supporting information, p. 428 - 432 (2020/01/31)
A catalyst-controlled highly chemoselective and regioselective intramolecular cycloamidation of triazol-1-ylbenzamides toward the synthesis of scarcely known heterocycles is reported. In the presence of a palladium catalyst, this cycloisomerization reacti
Novel fused 1,2,3-triazolo-benzodiazepine derivatives as potent anticonvulsant agents: design, synthesis, in vivo, and in silico evaluations
Shafie, Arefeh,Mohammadi-Khanaposhtani, Maryam,Asadi, Mehdi,Rahimi, Nastaran,Ranjbar, Parviz Rashidi,Ghasemi, Jahan B.,Larijani, Bagher,Mahdavi, Mohammad,Shafaroodi, Hamed,Dehpour, Ahmad Reza
, p. 179 - 189 (2019/03/26)
Abstract: A novel series of 1,2,3-triazolo-benzodiazepine derivatives 6a–o has been synthesized and evaluated in vivo for their anticonvulsant activities using by pentylenetetrazole (PTZ)- and maximal electroshock (MES)-induced seizures in mice. The synth
Telescoped synthesis of C3-functionalized (E)-arylamidines using Ugi-Mumm and regiospecific quinazolinone rearrangements
Jaffett, Victor A.,Nerurkar, Alok,Cao, Xufeng,Guzei, Ilia A.,Golden, Jennifer E.
supporting information, p. 3118 - 3128 (2019/03/26)
An efficient four-step, six-transformation protocol was developed to afford bioactive N-alkyl- or N-arylamide (E)-arylamidines featuring strategic amidine C3 modifications which were inaccessible or low yielding by previous methods. This synthetic approac
Fragment-Based Discovery of a Qualified Hit Targeting the Latency-Associated Nuclear Antigen of the Oncogenic Kaposi's Sarcoma-Associated Herpesvirus/Human Herpesvirus 8
Kirsch, Philine,Jakob, Valentin,Oberhausen, Kevin,Stein, Saskia C.,Cucarro, Ivano,Schulz, Thomas F.,Empting, Martin
, (2019/05/01)
The latency-associated nuclear antigen (LANA) is required for latent replication and persistence of Kaposi's sarcoma-associated herpesvirus/human herpesvirus 8. It acts via replicating and tethering the virus episome to the host chromatin and exerts other functions. We conceived a new approach for the discovery of antiviral drugs to inhibit the interaction between LANA and the viral genome. We applied a biophysical screening cascade and identified the first LANA binders from small, structurally diverse compound libraries. Starting from a fragment-sized scaffold, we generated optimized hits via fragment growing using a dedicated fluorescence-polarization-based assay as the structure-activity-relationship driver. We improved compound potency to the double-digit micromolar range. Importantly, we qualified the resulting hit through orthogonal methods employing EMSA, STD-NMR, and MST methodologies. This optimized hit provides an ideal starting point for subsequent hit-to-lead campaigns providing evident target-binding, suitable ligand efficiencies, and favorable physicochemical properties.
Fragment-Based Discovery of a Qualified Hit Targeting the Latency-Associated Nuclear Antigen of the Oncogenic Kaposi's Sarcoma-Associated Herpesvirus/Human Herpesvirus 8
Kirsch, Philine,Jakob, Valentin,Oberhausen, Kevin,Stein, Saskia C.,Cucarro, Ivano,Schulz, Thomas F.,Empting, Martin
, p. 3924 - 3939 (2019/05/06)
The latency-associated nuclear antigen (LANA) is required for latent replication and persistence of Kaposi's sarcoma-associated herpesvirus/human herpesvirus 8. It acts via replicating and tethering the virus episome to the host chromatin and exerts other functions. We conceived a new approach for the discovery of antiviral drugs to inhibit the interaction between LANA and the viral genome. We applied a biophysical screening cascade and identified the first LANA binders from small, structurally diverse compound libraries. Starting from a fragment-sized scaffold, we generated optimized hits via fragment growing using a dedicated fluorescence-polarization-based assay as the structure-activity-relationship driver. We improved compound potency to the double-digit micromolar range. Importantly, we qualified the resulting hit through orthogonal methods employing EMSA, STD-NMR, and MST methodologies. This optimized hit provides an ideal starting point for subsequent hit-to-lead campaigns providing evident target-binding, suitable ligand efficiencies, and favorable physicochemical properties.
