Diethyl 2-[(2-benzyl-1-phenyl­sulfonyl-1H-indol-3-yl)methyl­ene]malonate

In the title compound, C29H27NO6S, the sulfonyl-bound phenyl ring is almost perpendicular to the indole ring system [dihedral angle = 87.96 (6)°], while the benzyl­phenyl ring is oriented at an angle of 76.8 (7)°. An intra­molecular C—H⋯O hydrogen bond is observed. In the crystal structure, mol­ecules are linked into a zigzag C(10) chain along the b axis by inter­molecular C—H⋯O hydrogen bonds

32nd cyprus-noordwijkerhout-camerino symposium: Trends in drug research 2014

Sunshine & science: The 32nd Cyprus-Noordwijkerhout-Camerino Symposium on Trends in Drug Research took place in May 2014 in Limassol (Cyprus). This Conference Reports outlines the cutting edge science presented over the course of the symposium. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Synthesis of compounds as melatonin agonists and antagonists

The functions of melatonin, the hormone of the pineal gland, are of considerable current interest. Synthetic melatonin analogues as agonists and antagonists have been explored in some detail and the molecule can be considered as consisting of an indole core, acting mainly as a spacer, and the 5-methoxyl and 3-amidoethyl side chains acting as the functional components, as originally proposed by Heward and Hadley. This review focuses on the synthetic routes to these melatonin analogues, first of the core, then of the substituents that have teen attached to the core, and finally those compounds with restricted conformations and those that are chiral. The importance of the various factors involved in the activity of the compounds as agonist or antagonists is indicated, as is the difference in activity of enantiomers. © 2007 Bentham Science Publishers Ltd

Melatonin receptor antagonist luzindole: A facile new synthesis

A new, convenient and high yield route to luzindole, the most commonly used melatonin receptor antagonist, is described. The new method involves the Sonogashira coupling reaction between 2-iodoaniline and 3-phenyl-1-propyne followed by cyclisation of the adduct formed, C-3 indole nitroolefination with 1-(dimethylamino)-2-nitroethylene/TFA, reduction to the respective tryptamine and finally acetylation. © 2008 Bentham Science Publishers Ltd

An intriguing, regioselective synthesis of novel 2-(1-adamantylmethyl) tetrahydropyridines

Treatment of piperidine 8 with acetyl chloride or ethyl chloroformate in the presence of triethylamine gave the 2,3-dehydrogenated products 10a and 10b, respectively, together with the expected N-acylpiperidines 9. © 2008 Bentham Science Publishers Ltd

Design and synthesis of potent N1-substituted indole melatonin receptor agonists

The design and expeditious synthesis of two new indole analogs with up to 5-fold potency of that of melatonin is described. © 2003 The Royal Society of Chemistry

Design and synthesis of new N1 and C3-substituted 4-fluoroindolic melatoninergics

A series of new C-3 and N1-substituted 4-fluorotryptamides have been prepared and tested for their ability to activate pigment granule aggregation in Xenopus laevis melanophores and bind to the recombinant human MT1 and MT2 melatonin receptor subtypes expressed in NIH 3T3 cells. Planar sp2 geometry at C-3-βC seems to decrease the population of the preferred conformation as it renders 4-fluoroindoles 4b-d weaker antagonists than their C-3-βC-unsubstituted congeners 3a-e. This effect is not preclusively linked with the C-3 region, as the same geometry around N1 (compounds 5a-c) similarly leads to weak antagonistic action. Last, the new C-3 substituted 4-fluorotryptamides presented herein are substantially more potent than their respective N-OMe functionalized congeners, previously reported. © 2007 Bentham Science Publishers Ltd

New pyrazole-annulated azathioxanthenes as potential intercalators: Synthesis and structure elucidation

As part of our program aiming at developing efficacious intercalating agents, a new series of pyrazole-annulated azathioxanthenes 15a-e has been synthesized. Structure elucidation of 15a-e was based on their spectral data and especially the NOESY nmr spectrum of analog 15a