Synthesis of some pyrimido[4′,5′:4,5]thieno[2,3‐<i>b</i>]quinolines and related heterocycles

Hafez, Ali A. Abdel; El-Dean, Adel Kamal; Hassan, A. A.; El‐Kashef, Hussein; Rault, Syl­vain; Robba, M.

doi:10.1002/jhet.5570330236

Cited by 28 publications

(5 citation statements)

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“…Some of the most interesting derivatives of thiophenes are 3-aminothieno[2,3- b ]pyridines, in view of their wide spectrum of high biological activities and valuable pro-perties in many applications [ 202 , 203 , 204 ]. It is noteworthy that investigators [ 205 , 206 , 207 , 208 , 209 , 210 , 211 , 212 , 213 , 214 , 215 , 216 , 217 , 218 , 219 , 220 , 221 , 222 , 223 , 224 , 225 , 226 , 227 , 228 , 229 ] have de-voted considerable attention in recent years to the synthesis of thieno[2,3- b ]pyridines 101 via S -alkylation of 3-cyanopyridine-2(1 H )-thiones 99 with α-haloketones ( Scheme 28 ).…”

Section: Reactions Of α-Haloketones With Oxygen Nitrogen and Sulfmentioning

confidence: 99%

The Chemistry of α-Haloketones and Their Utility in Heterocyclic Synthesis

2003

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Section: Reactions Of α-Haloketones With Oxygen Nitrogen and Sulfmentioning

confidence: 99%

The Chemistry of α-Haloketones and Their Utility in Heterocyclic Synthesis

2003

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“…Typical for the established alkylation of 3-unsubstitutedthienopyrimidin-4-ones [26][27][28], compound 4a reacted readily with ethyl chloroacetate in DMF in the presence of potassium carbonate to afford the target N-alkylated product, 4c. All spectroscopic data fitted perfectly with the proposed structure 4 (see Experimental section).…”

Section: Chemistrymentioning

confidence: 99%

Antimicrobial investigations on synthetic p-tolylazo derivatives of thienopyrimidinone based on an ortho funtionalized thiophene nucleus

2010

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KEYWORDSNew derivatives of thieno [2,3-d]pyrimidin-4-one, 4ac, and 6 were respectively synthezised based on thiophene derivative, 2c, bearing ortho-disposed amino and ester groups. Carbohydrazide, 7, was obtained by hydrazinolysis of 3-ethoxycabonylmethyl derivative, 4c. Compounds 4b and 7 were used to build up two series of novel 3-substitutedmethylthieno[2,3-d]pyrimidin-4-ones, 711, and their corresponding 3-substituted-amino analogues 12, 15a,b, 18, which were of significant interest for biological study. The new thieno[2,3-d]pyrimidin-4-one derivatives, with various groups in position 3, were screened for their preliminary antimicrobial activity against a representative panel of Gram-positive and Gram-negative bacteria as well as fungi strains. The compounds tested displayed different levels of antibacterial and antifungal effects, with the assays carried out on six pathogenic bacteria and six pathogenic fungi. Of these compounds, the 3-unsubstituted-thieno[2,3d]pyrimidin-4(3H)-one, 4a, showed the lowest effect on pathogenic bacteria, while the corresponding 3-substituted analogues produced inhibitory effects against bacteria similar or superior to the reference drug Tetracycline. For those derivatives of thieno[2,3-d]pyrimidin-4one in which the 3-position contains a methylene moiety, it has been observed that the antibacterial effect was in general found to be significantly higher than the corresponding analogues with a substituted-amino moiety in position 3. Despite promising in vitro antibacterial activity of the new thienopyrimidin-4-ones, only compounds 7, 10 and 11, among the compounds tested, exhibited some kind of antifungal activity. The detailed synthesis and biological screening data were reported.Thienopyrimidinone Aminoformylation Acetylation Hydrazinolysis Antimicrobial activity

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“…The reaction of 9 and the diene at room temperature gave a mixture of regioisomers, methyl 3-diacetylamino-5-trimethylsilyloxy-4,9-dioxo-4,4a,5,8,8a,9-hexahydronaphtho [2,3- Heterocyclisation of compound 5 to 6,9-dimethoxy-4H- (15) was attempted by reaction with sodium hydroxide, followed by reaction of the resulting sodium carboxylate with acetic anhydride using a reported methodology. 18) The treatment provided heterocycle (15) and all attempts to obtain quinone 16 by oxidative demethylation of 15 with CAN were unsuccessful and the starting material was recovered in these experiments (Chart 4).…”

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confidence: 99%

Studies on Quinones. Part 37. Synthesis and Biological Activity of o-Aminoester Functionalised Benzo- and Naphtho[2,3-b]-thiophenequinones.

Valderrama

Astudillo

Tapia

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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Natural and synthetic quinonoid compounds are wellknown substances which possess a variety of biological properties such as antibacterial, antifungal, antiprotozoal, inhibition of the human immunodeficiency virus (HIV)-1 reverse transcriptase and antitumor activity.2-7) Some of these pharmacological effects have been attributed to the formation of DNA-damaging anion-radical intermediates formed by bioreduction of the quinone nucleus.8) Among heterocyclic quinones with cytotoxic activity, those containing a thiophene nucleus fused to a quinone system have received little attention 9,10) despite the antitumoral activity of thiophene analogues of daunomycin and mitoxantrone. 11,12) As part of a program directed towards the design and synthesis of carbo-and heterocyclic quinones as potential antiprotozoal agents, we have reported the synthesis and antiprotozoal activity of benzopyrano-and benzo [b]thiophenequinones. 1,13,14) Since the thiophene ring-containing quinones showed promising antiprotozoal activity against trypanosome cruzi and strains of Leishmania spp.1,14) we decided to continue the studies on synthesis and biological evaluation of new members of this series containing functional groups on C-2 and C-3 positions of the thiophene ring.This paper describes the preparation of functionalised benzo [b]thiophenes and their application to the synthesis of benzo-and naphthothiophenequinones with orthoaminoester functionality on the thiophene ring. Moreover we report the cytotoxic activity of the new quinones against Leishmania amazonensis and human-T-cell leukemia virus type 1 (HTLV-I), the causative agent of two well-defined diseases: adult T-cell leukemia/lymphoma (ATLL) and tropical spastic paraparesis/HTLV-1 associated myelopathy (TSP/ HAM). 15)In a previous work we have described the synthesis of a variety of 2-substituted benzo [b]thiophene-4,7-quinones using a two step sequence which involves the reaction of dimethoxy-o-acylnitroarenes with methyl thioglycolate followed by oxidative deprotection of the corresponding dimethoxybenzo[b]thiophene with ceric ammonium nitrate (CAN).16) On the basis of these results we investigated the synthesis of ortho-aminoesters 5 via cyclisation of 3,6-dimethoxy-2-nitrobenzonitrile (3) with methyl thioglycolate. Compound 5 could be a valuable intermediate in the synthesis of angular tetracyclic thiophene-containing quinones due to the possibility to extend the bicyclic system through either the thiophene and/or the quinone rings.3,6-Dimethoxy-2-nitrobenzaldehyde (1), prepared as reported, 17) was converted into 2,5-dimethoxy-6-nitrobenzonitrile (3) in 54% total yield, by reaction with hydroxylamine followed by dehydration of 3,6-dimethoxy-2-nitrobenzaldehyde oxime (2) with acetic anhydride. The thiophene ring formation on 3 was attempted by reaction with methyl thioglycolate in N,N-dimethylformamide (DMF) using potassium carbonate however, methyl (2-cyano-3,6-dimethoxyphenylsulfanyl)acetate (4) was isolated as the main product along with small amounts of the methyl 3-amino-...

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Synthesis of some pyrimido[4′,5′:4,5]thieno[2,3‐b]quinolines and related heterocycles

Cited by 28 publications

References 5 publications

The Chemistry of α-Haloketones and Their Utility in Heterocyclic Synthesis

The Chemistry of α-Haloketones and Their Utility in Heterocyclic Synthesis

Antimicrobial investigations on synthetic p-tolylazo derivatives of thienopyrimidinone based on an ortho funtionalized thiophene nucleus

Studies on Quinones. Part 37. Synthesis and Biological Activity of o-Aminoester Functionalised Benzo- and Naphtho[2,3-b]-thiophenequinones.

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