Peptídeos de conformação restrita induzida pela incorporação de unidades (aza)lactâmicas

Pohlmann, Adriana Raffin; Quirion, J.‐C.; Guillaume, Dominique; Husson, Henri‐Philippe

doi:10.1590/s0100-40421999000600010

Quím. Nova

1999

DOI: 10.1590/s0100-40421999000600010

|View full text |Cite

Peptídeos de conformação restrita induzida pela incorporação de unidades (aza)lactâmicas

Adriana Raffin Pohlmann¹,

J.‐C. Quirion²,

Dominique Guillaume³

et al.

Abstract: Recebido em 21/8/98; aceito em 29/1/99 CONFORMATIONALLY CONSTRAINED INDUCED PEPTIDES CONTAINING (AZA)LACTAM UNITS. Conformational constraint is an approach which can be used to restrict the flexibility of peptide molecules and to provide information on the topographical requirements of receptors. The incorporation of conformationally constrained units in a peptide can lead to peptide analogues that present numerous advantages such as the potentialization of the pharmacological activity and the decrease of enzy… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2003

2018

Publication Types

Select...

Article4

Relationship

Self Cite1

Independent3

Authors

Journals

Cited by 4 publications

References 39 publications

(53 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

New 1,3-benzodioxole derivatives: Synthesis, evaluation of in vitro schistosomicidal activity and ultrastructural analysis

Silva

Oliveira

Silva

et al. 2018

Chemico-Biological Interactions

View full text Add to dashboard Cite

Schistosomiasis is considered a serious public health problem in 78 countries and territories located in Africa, Asia and America and it is estimated in more than 249 million people infected by any of the species of Schistosoma. The exclusive use of praziquantel (PZQ), effective drug against all species of Schistosoma, has been the basis of the development of a possible resistance against the strains of this parasite. In addition, PZQ is not effective against young forms of worms. Thus, there is a need for the development of new drugs with schistosomicidal activity. The objective of this work was to synthesize and to evaluate the therapeutic potential of new benzodioxole derivatives (3-14) candidates for schistosomicidal drugs. All compounds synthesized showed in vitro schistosomicidal activity. The derivative 12 was considered the best compound, since it took 100% of worms to mortality in the first 72 h of exposure at the concentration of 100 μM and 83.3% at the concentration of 50 μM. Furthermore, male and female adult worms, incubated for 24 h with the compound 12 showed tegument damages characterized by extensive desquamation and edema, tuber destruction, bubble formation and exposure of the muscle layer. This compound has a restricted structure, where the thiazolidinone is attached to the 4-position of the 1,3-benzodioxol ring. The structural conformation of derivative 12 was probably responsible for the promising schistosomicidal activity, where the presence of an electron/conformational restriction of the thiazolidine ring, as well as the action of bromine as a bulk substitute, favored an increase in biological activity. In addition, tegumentary changes caused by derivative 12 may also have been responsible for the death of adult worms of Schistosoma mansoni. Therefore, we verified that the results obtained in this study make benzodioxole derivatives possible candidates for prototypes of new schistosomicidal drugs.

show abstract

New 1,3-benzodioxole derivatives: Synthesis, evaluation of in vitro schistosomicidal activity and ultrastructural analysis

Silva

Oliveira

Silva

et al. 2018

Chemico-Biological Interactions

View full text Add to dashboard Cite

show abstract

Peptide analogs containing the pentacyclo[5,4,0,02,6,03,6,05,9]undecane scaffold: conformational analysis in solution

Axt

Oulyadi²,

Pannecoucke³

et al. 2004

Journal of Molecular Structure

View full text Add to dashboard Cite

Studies on Intramolecular Diels−Alder Reactions of Furo[3,4-c]pyridines in the Synthesis of Conformationally Restricted Analogues of Nicotine and Anabasine

et al. 2003

View full text Add to dashboard Cite

En route to conformationally restricted analogues of nicotine and anabasine, a novel synthetic route to bridged anabasines is described that hinges on a domino intramolecular [4 + 2]-cycloaddition/ring opening-elimination sequence of 3-amino-substituted furo[3,4-c]pyridines. Extension of this route to bridged nicotines, however, proved abortive, even when the dienophile tether is activated by a p-tolylsulfonyl group or when the diene moiety is activated by an electron-releasing methoxy substituent. A detailed density functional theoretical study (B3LYP/6-31+G) was undertaken to provide insight into the factors that facilitate an intramolecular Diels-Alder reaction in the former case.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Peptídeos de conformação restrita induzida pela incorporação de unidades (aza)lactâmicas

Cited by 4 publications

References 39 publications

New 1,3-benzodioxole derivatives: Synthesis, evaluation of in vitro schistosomicidal activity and ultrastructural analysis

New 1,3-benzodioxole derivatives: Synthesis, evaluation of in vitro schistosomicidal activity and ultrastructural analysis

Peptide analogs containing the pentacyclo[5,4,0,02,6,03,6,05,9]undecane scaffold: conformational analysis in solution

Studies on Intramolecular Diels−Alder Reactions of Furo[3,4-c]pyridines in the Synthesis of Conformationally Restricted Analogues of Nicotine and Anabasine

Contact Info

Product

Resources

About