Synthesis and preliminary pharmacological evaluation of thiophene analogues of viloxazine as potentialantidepressant drugs

Corral, Carlos; Lissavetzky, J.; Manzanares, Ignacio; Darias, V.; Expósito-Orta, M.Auxiliadora; Conde, José A. Martı́n; Sánchez-Mateo, Candelaria C.

doi:10.1016/s0968-0896(99)00070-x

Cited by 24 publications

(12 citation statements)

References 13 publications

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“…Our idea was the possibility of change in the core of this class of peptidomimetics by replacing of the phenyl ring with a heterocyclic ring, namely thiophene or benzothiophene: In fact it is well known that a thienyl ring mimics a phenyl group of phenylalanine in peptidomimetics [8] and in many drugs [9,10,11]. …”

Section: Peptidomimetic Structuresmentioning

confidence: 99%

Heterocycles in Peptidomimetics and Pseudopeptides: Design and Synthesis

et al. 2012

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Section: Peptidomimetic Structuresmentioning

confidence: 99%

Heterocycles in Peptidomimetics and Pseudopeptides: Design and Synthesis

et al. 2012

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“…12 It is known that the biological half-life of antidepressant drugs such as viloxazine became longer when the benzene ring is replaced by thiophene. 13 It is also observed that the thienyl ring mimics the phenyl group of phenylalanine in peptidomimetics, 14 in many drugs. 15,16 Currently, a number of non-steroidal anti-inflammatory drugs (NSAIDs) containing thiophene ring such as Tiaprofenic acid (a) and Tenidap (b) ( Figure 1) are available for the treatment of pain and inflammatory disorders.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and docking studies of thiophene scaffolds in COX-2

Singh¹,

Sharma²,

Bisetty³

et al. 2011

Arkivoc

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A series of new thiophene compounds 6a-6l was synthesized from the reactions of in situ generated cross-conjugated enaminothiones 2 and α-bromoketones/ethyl bromoacetate. Moreover, the synthesis of 1,3-thiazine 12 and functionalized thiopyran 18 heterocycles from the cycloaddition reactions of N,N'-bis[(dimethylamino)methylene]thiourea 9, is also described. Additionally, the binding conformations of these compounds 6a-6l and some anti-inflammatory drugs (NSAIDs) were determined by their docking in the active site of the Cyclooxygenase-2 (COX-2) enzyme.

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“…Moreover, thiophene moiety is a well known as isostere for benzene; for example, the replacement of benzene ring of the antidepressant drug, Viloxazine (I, Fig. 1), by thiophene one led to a prolongation of half-life [5]. Also, the quinoline ring system is well known as an important structural unit widely existing in alkaloids, therapeutics, and synthetic analogues with interesting biological activities [6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of New Heterocyclic Compounds Containing Thienylbenzo[h]Quinoline Moiety

Al‐Taifi

Abbady

Bakhite

2015

Journal of Heterocyclic Chem

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In this paper the reaction of 2‐(2′‐thienylmethylene)‐3,4‐dihydronaphthalen‐2(1H)‐one (1) with cyanothioacetamide gave a mixture of 3‐cyano‐5,6‐dihydro‐4‐(2′‐thienyl)‐benzo[h]quinolin‐2(1H)‐thione (2) and the related disulfide 3. Compound 2 was reacted with some halo compounds namely; ethyl chloroacetate, chloroacetamide, chloro(N‐(p‐chlorophenyl))acetamide, N1‐chloroacetylsulfanilamide, and 2‐chloromethyl‐1H‐benzimidazole to produce a series of 2‐(substituted)methylthio‐3‐cyano‐5,6‐dihydro‐4‐(2′‐thienyl)benzo[h]quinolines 4a, 4b, 4c, 4d, 4e and 11. Upon heating the latter compounds with sodium ethoxide, they underwent intramolecular Thorpe–Zeigler cyclization to furnish the corresponding 2‐(substituted)‐3‐amino‐5,6‐dihydro‐4‐(2′‐thienyl)‐benzo[h]thieno[2,3‐b]quinolines 5a, 5b, 5c, 5d, 5e and 12. (3‐Cyano‐5,6‐dihydro‐4‐(2′‐thienyl)‐benzo[h]quinolin‐2‐ylthio)acethydrazide (8) and the related isomer, 3‐amino‐5,6‐dihydro‐4‐(2′‐thienyl)thieno[2,3‐b]benzo[h]quinoline‐2‐carbohydrazide (9), were also synthesized. Most of the aforementioned compounds were used as key intermediates for synthesizing other benzo[h]quinolines, benzo[h]thieno[2,3‐b]quinolines as well as benzo[h]pyrimido[4′,5′:4,5] thieno[2,3‐b]quinolines. The structure of all synthesized compounds was confirmed by spectroscopic measurements and analytical analyses.

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Synthesis and preliminary pharmacological evaluation of thiophene analogues of viloxazine as potentialantidepressant drugs

Cited by 24 publications

References 13 publications

Heterocycles in Peptidomimetics and Pseudopeptides: Design and Synthesis

Heterocycles in Peptidomimetics and Pseudopeptides: Design and Synthesis

Synthesis and docking studies of thiophene scaffolds in COX-2

Synthesis and Characterization of New Heterocyclic Compounds Containing Thienylbenzo[h]Quinoline Moiety

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