Corrigendum to “Benzylpiperidine variations on histamine H3 receptor ligands for improved drug-likeness” [Bioorg. Med. Chem. Lett. 24 (2014) 2236–2239]

Wingen, Kerstin; Schwed, J. Stephan; Isensee, Kathleen; Weizel, Lilia; Živković, Aleksandra; Odadzic, Dalibor; Stark, Holger

doi:10.1016/j.bmcl.2014.04.086

Cited by 3 publications

(2 citation statements)

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“…Structure of synthesized molecules was drawn by using Chem Draw. [41,42] Energy minimization protocol and macro molecular force field was used to perform Ligand optimization. [39] Different ligand conformations were produced on the basis of their dihedral energy, bond energy, initial potential energy, CHARM energy values.…”

Section: Molecular Dockingmentioning

confidence: 99%

Synthesis, biological screening, in silico study and fingerprint applications of novel 1, 2, 4‐triazole derivatives

Khan

Sreenivasa

Govindaiah

et al. 2020

Journal of Heterocyclic Chem

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A series of novel 1,2,4 triazole derivatives were synthesized by treating 4‐bromo‐2‐(4H‐1,2,4‐triazole‐3‐yl)aniline (4) with different substituted benzene sulfonyl chlorides 5(a‐f) and benzyl bromides 7(a‐e). IR, 1H‐NMR, 13C‐NMR, and mass analysis confirmed the structures of the newly synthesized compounds. All derivatives were screened for their in vitro antibacterial activity against two bacterial strains viz Escherichia coli and Staphylococcus aureus, antifungal activity against Aspergillus flavus and Candida albicans, anthelmintic activity against Pheretima posthuma and also cytotoxicity activity against MDA‐MB 231 and A375 cancer cell lines. It was found that some of the derivatives showed significant antibacterial, antifungal, anthelmintic, and cytotoxic activities when compared to respective standard drugs. Molecular docking studies have assisted the theoretical binding mode of the target molecules. Compounds were also explored for fingerprint application.

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Section: Molecular Dockingmentioning

confidence: 99%

Synthesis, biological screening, in silico study and fingerprint applications of novel 1, 2, 4‐triazole derivatives

Khan

Sreenivasa

Govindaiah

et al. 2020

Journal of Heterocyclic Chem

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“…In the past, [23–26] researchers have demonstrated that improved PK profiles can be obtained by tuning/modulating the physical properties like lipophilicity (LogP, LogD) of H 3 R ligands, resulting in reduced tissue retention time and shorter half‐life (t 1/2 ) in vivo .…”

Section: Introductionmentioning

confidence: 99%

1‐[2‐(1‐Cyclobutylpiperidin‐4‐yloxy)‐6,7‐dihydro‐4H‐thiazolo[5,4‐c]pyridin‐5‐yl]propan‐1‐one: a Histamine H₃ Receptor Inverse Agonist with Efficacy in Animal Models of Cognition

et al. 2021

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A series of chemical optimizations, which was guided by in vitro affinity at histamine H 3 receptor (H 3 R), modulation of lipophilicity, ADME properties and preclinical efficacy resulted in the identification of 1-[2-(1-cyclobutylpiperidin-4-yloxy)-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl]propan-1-one (45 e) as a potent and selective (K i = 4.0 nM) H 3 R inverse agonist. Dipsogenia induced by (R)-α-methylhistamine was dose dependently antagonized by 45 e, confirming its functional antagonism at H 3 R. It is devoid of hERG and phospholipidosis issues. Compound 45 e has adequate oral exposures and favorable half-life in both rats and dogs. It has demonstrated high receptor occupancy (ED 80 = 0.22 mg/kg) and robust efficacy in object recognition task and, dose dependently increased acetylcholine levels in brain. The sub-therapeutic doses of 45 e in combination with donepezil significantly increased acetylcholine levels. The potent affinity, selectivity, in vivo efficacy and drug like properties together with safety, warrant for further development of this molecule for potential treatment of cognitive disorders associated with Alzheimer's disease.

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Synthesis, Anti-inflammatory Activity and in silico Studies of Some Novel Morpholine Based Carboxamides

et al. 2020

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Two series of carboxamides were synthesized from 3-fluoro-4-morpholinoaniline and different substituted aromatic/heterocyclic carboxylic acids. All the compounds were characterized by IR, 1H NMR, 13C NMR and mass spectral data. The newly synthesized amide derivatives were screened for anti-inflammatory activity by following carrageenan induced rat paw edema method. Among the compounds screened, compound 6e was found to be highly potent. Molecular docking interaction of active compounds revealed that effective binding was observed in the pocket of COX-I and COX-II proteins.

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Corrigendum to “Benzylpiperidine variations on histamine H3 receptor ligands for improved drug-likeness” [Bioorg. Med. Chem. Lett. 24 (2014) 2236–2239]

Cited by 3 publications

References 0 publications

Synthesis, biological screening, in silico study and fingerprint applications of novel 1, 2, 4‐triazole derivatives

Synthesis, biological screening, in silico study and fingerprint applications of novel 1, 2, 4‐triazole derivatives

1‐[2‐(1‐Cyclobutylpiperidin‐4‐yloxy)‐6,7‐dihydro‐4H‐thiazolo[5,4‐c]pyridin‐5‐yl]propan‐1‐one: a Histamine H₃ Receptor Inverse Agonist with Efficacy in Animal Models of Cognition

Synthesis, Anti-inflammatory Activity and in silico Studies of Some Novel Morpholine Based Carboxamides

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Corrigendum to “Benzylpiperidine variations on histamine H3 receptor ligands for improved drug-likeness” [Bioorg. Med. Chem. Lett. 24 (2014) 2236–2239]

Cited by 3 publications

References 0 publications

Synthesis, biological screening, in silico study and fingerprint applications of novel 1, 2, 4‐triazole derivatives

Synthesis, biological screening, in silico study and fingerprint applications of novel 1, 2, 4‐triazole derivatives

1‐[2‐(1‐Cyclobutylpiperidin‐4‐yloxy)‐6,7‐dihydro‐4H‐thiazolo[5,4‐c]pyridin‐5‐yl]propan‐1‐one: a Histamine H3 Receptor Inverse Agonist with Efficacy in Animal Models of Cognition

Synthesis, Anti-inflammatory Activity and in silico Studies of Some Novel Morpholine Based Carboxamides

Contact Info

Product

Resources

About

1‐[2‐(1‐Cyclobutylpiperidin‐4‐yloxy)‐6,7‐dihydro‐4H‐thiazolo[5,4‐c]pyridin‐5‐yl]propan‐1‐one: a Histamine H₃ Receptor Inverse Agonist with Efficacy in Animal Models of Cognition