Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors

Carocci, Alessia; Catalano, Alessia; Lovece, Angelo; Lentini, Giovanni; Duranti, Andrea; Lucini, Valeria; Pannacci, Marilou; Scaglione, Francesco; Franchini, Carlo

doi:10.1016/j.bmc.2010.06.100

Cited by 34 publications

(19 citation statements)

References 55 publications

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“…Compounds 1k , 1m , 1o were prepared as reported in Scheme . Benzyl alcohols 5k , 5m , 5o were reacted with 4‐nitrophenol under Mitsunobu conditions to give their nitro derivatives 6k , 6m , 6o , which were reduced by catalytic hydrogenation to anilines 7k , 7m , 7o . 2‐Aminobenzothiazole derivatives 1k , 1m , 1o were prepared via thiocyanation of 7k , 7m , 7o .…”

Section: Resultsmentioning

confidence: 99%

1,3-Benzothiazoles as Antimicrobial Agents

Defrenza

Catalano

Carocci

et al. 2014

J. Heterocyclic Chem.

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Starting from 2‐amino‐1,3‐mercaptobenzothiazoles recently reported (1a, 1b, 1c, 1d, 1e, 1f, 1g, 1h), a series of the corresponding 2‐mercapto‐1,3‐benzothiazole isosters (2a, 2b, 2c, 2d, 2e, 2f, 2g, 2h) were screened for their in vitro antibacterial and antifungal activities. Results underline that the presence of the mercapto moiety at the 2‐position of the heterocyclic nucleus is crucial for activity against bacteria. The biological screening against Candida spp. identified commercial 2f as the most promising compound as antifungal against Candida albicans and tropicalis. Molecular modeling studies supported these results. Then, to enlarge structure‐activity relationship (SAR) studies on series 1, newly synthesized compounds (1k, 1l, 1m, 1n, 1o, 1p) were reported. All the compounds belonging to this series and bearing a bulky substituent at the 6‐position of the aryl moiety showed high antifungal activity.

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Section: Resultsmentioning

confidence: 99%

1,3-Benzothiazoles as Antimicrobial Agents

Defrenza

Catalano

Carocci

et al. 2014

J. Heterocyclic Chem.

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“…TLC analyses were performed on precoated silica gel on aluminum sheets (Kieselgel 60 F 254 , Merck). GC analyses were performed on a Varian 3800 gas chromatograph equipped with a flame ionization detector and a Jew Scientific DB-5 capillary column (30 m length × 0.25 mm ID, 0.25 m film thickness) [42].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of a New Series of N‐1,3‐Benzothiazol‐2‐ylbenzamides

Armenise

Carocci

Catalano

et al. 2013

Journal of Chemistry

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Enterococcus faecalisis a Gram-positive commensal inhabitant of the intestinal tract of humans, animals, and insects. However, it is also an opportunistic pathogen and has emerged as a leading cause of hospital-acquired extraintestinal infections. Fluoroquinolones have been frequently used to treatE. faecalisinfections, and the emergence of fluoroquinolone-resistantE. faecalisstrains has recently been reported in several countries. Thus, the identifications of new antibiotics specifically directed toE. faecalismay be envisaged. In this paper, a new series ofN-1,3-benzothiazol-2-ylbenzamides have been designed, synthesized, and evaluated for theirin vitroantimicrobial activities. Among the tested compounds,3iwas active againstE. faecalis.

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“…Actually, 4-azamelatonin (Figure 3-1) has shown identical MT 1 ( K i =0.24 nM) and MT 2 ( K i =0.36 nM) binding affinities to MLT, for receptors expressed in HEK-293 cells,93 while indene (Figure 3-2) showed indeed five to ten times higher affinities than MLT, in both receptor subtypes, expressed in CHO cells 94. Moreover, regarding bioisosteric substitutions of the indole nucleus, a series of chiral phenoxyalkyl and phenylthioalkyl amides have been always reported 95. This study provided compounds with nanomolar affinity for both MLT receptor subtypes, expressed in NIH3T3 cells.…”

Section: Melatonergic Ligands In Developmentmentioning

confidence: 92%

Melatonergic drugs in development

Carocci¹,

Catalano²,

Sinicropi³

2014

CPAA

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Melatonin (N-acetyl-5-methoxytryptamine) is widely known as “the darkness hormone”. It is a major chronobiological regulator involved in circadian phasing and sleep-wake cycle in humans. Numerous other functions, including cyto/neuroprotection, immune modulation, and energy metabolism have been ascribed to melatonin. A variety of studies have revealed a role for melatonin and its receptors in different pathophysiological conditions. However, the suitability of melatonin as a drug is limited because of its short half-life, poor oral bioavailability, and ubiquitous action. Due to the therapeutic potential of melatonin in a wide variety of clinical conditions, the development of new agents able to interact selectively with melatonin receptors has become an area of great interest during the last decade. Therefore, the field of melatonergic receptor agonists comprises a great number of structurally different chemical entities, which range from indolic to nonindolic compounds. Melatonergic agonists are suitable for sleep disturbances, neuropsychiatric disorders related to circadian dysphasing, and metabolic diseases associated with insulin resistance. The results of preclinical studies on animal models show that melatonin receptor agonists can be considered promising agents for the treatment of central nervous system-related pathologies. An overview of recent advances in the field of investigational melatonergic drugs will be presented in this review.

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Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors

Cited by 34 publications

References 55 publications

1,3-Benzothiazoles as Antimicrobial Agents

1,3-Benzothiazoles as Antimicrobial Agents

Synthesis and Antimicrobial Evaluation of a New Series of N‐1,3‐Benzothiazol‐2‐ylbenzamides

Melatonergic drugs in development

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