Synthesis and biological evaluation of novel piperidine-benzodioxole derivatives designed as potential leishmanicidal drug candidates

Fernandes, Ítalo Antônio; Almeida, Letícia de; Ferreira, Patrícia Espuri; Marques, Marcos José; Rocha, Raíssa Prado; Coelho, Luiz Felipe Leomil; Carvalho, Diogo Teixeira; Viegas, Cláudio

doi:10.1016/j.bmcl.2015.05.068

Cited by 9 publications

(5 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…With the aim of introducing a longer spacer between the pyrrolidine and the porphyrin moieties, we synthesized the N -Boc-protected bicyclic aldehyde 11 by direct reductive amination [ 27 ] between 4-(hydroxymethyl)piperidine 9 [ 28 ] and N -Boc-( S )-prolinal 4 , followed by Swern oxidation of the intermediate alcohol 10 ( Scheme 4 ).…”

Section: Resultsmentioning

confidence: 99%

Chiral Amphiphilic Secondary Amine-Porphyrin Hybrids for Aqueous Organocatalysis

et al. 2020

View full text Add to dashboard Cite

Two chiral proline-derived amphiphilic 5-substituted-10,15,20-tris(4-sulfonatophenyl)porphyrins were prepared, and their pH-dependent supramolecular behavior was studied. In neutral aqueous solutions, the free-base form of the hybrids is highly soluble, allowing enamine-based organocatalysis to take place, whereas under acidic conditions, the porphyrinic protonated core of the hybrid leads to the formation of self-assembled structures, so that the hybrids flocculate and their catalytic activity is fully suppressed. The low degree of chirality transfer observed for aqueous Michael and aldol reactions strongly suggests that these reactions take place under true “in water” organocatalytic conditions. The highly insoluble catalyst aggregates can easily be separated from the reaction products by centrifugation of the acidic reaction mixtures, and after neutralization and desalting, the sodium salts of the sulfonated amine-porphyrin hybrids, retaining their full catalytic activity, can be recovered in high yield.

show abstract

Section: Resultsmentioning

confidence: 99%

Chiral Amphiphilic Secondary Amine-Porphyrin Hybrids for Aqueous Organocatalysis

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Many compound classes have exhibited activity in vitro against promastigotes or amastigotes, including thiophene-indole hybrids [82,83], 2-amino-thiophene derivatives [84], pyrazolothiophene hybrids [85], camphor hydrazone derivatives [86], tetroxanes [87], isoxazole derivatives and tetrahydrofuran neolignans [88], piperine derivatives [89], naphthotriazolyl-4-oxoquinolines [90], furazolidone-based cyclodextrins [91], 2-pyrimidinyl-hydrazone and N-acylhydrazone derivatives [92], piperidine-benzodioxole derivatives [93], and methyl gallate [94]. In vivo studies of these compounds are required to elucidate their activity and safety profiles before clinical development can begin.…”

Section: Drug Discovery Targeting a Single Leishmania Speciesmentioning

confidence: 99%

Drug Discovery for Cutaneous Leishmaniasis: A Review of Developments in the Past 15 Years

Corman,

McNamara,

Bakowski

2023

Microorganisms

View full text Add to dashboard Cite

Leishmaniasis is a group of vector-borne, parasitic diseases caused by over 20 species of the protozoan Leishmania spp. The three major disease classifications, cutaneous, visceral, and mucocutaneous, have a range of clinical manifestations from self-healing skin lesions to hepatosplenomegaly and mucosal membrane damage to fatality. As a neglected tropical disease, leishmaniasis represents a major international health challenge, with nearly 350 million people living at risk of infection a year. The current chemotherapeutics used to treat leishmaniasis have harsh side effects, prolonged and costly treatment regimens, as well as emerging drug resistance, and are predominantly used for the treatment of visceral leishmaniasis. There is an undeniable need for the identification and development of novel chemotherapeutics targeting cutaneous leishmaniasis (CL), largely ignored by concerted drug development efforts. CL is mostly non-lethal and the most common presentation of this disease, with nearly 1 million new cases reported annually. Recognizing this unaddressed need, substantial yet fragmented progress in early drug discovery efforts for CL has occurred in the past 15 years and was outlined in this review. However, further work needs to be carried out to advance early discovery candidates towards the clinic. Importantly, there is a paucity of investment in the translation and development of therapies for CL, limiting the emergence of viable solutions to deal with this serious and complex international health problem.

show abstract

“…In society prescription, this plant is shown for the treatment of obstruction, sleep deprivation, uneasiness, epilepsy, jungle fever, looseness of the bowels and cerebral pain [77]. S. spectabilis is an imperative wellspring of piperidine alkaloids with leishmanicidal movement [78,79]. Piperidine is a critical pharmacophore, a special framework and a magnificent heterocyclic framework in the field of medication revelation which gives various open doors in considering/investigating this moiety as an anticancer operator by following up on different receptors of most extreme significance.…”

Section: Pyrrole: Stachydrinementioning

confidence: 99%

Chemistry of Secondary Metabolites

Mohiuddin¹

2019

ACT

View full text Add to dashboard Cite

Medicinal plants, are known to deliver a wide scope of Plant Secondary Metabolites (PSMs) connected as bug sprays, medications, colors and poisons in farming, prescription, industry and biofighting in addition to bio-fear mongering, separately. Be that as it may, creation of PSMs is for the most part in little amounts, so we have to discover novel approaches to increment both amount and nature of them. Luckily, biotechnology proposes a few choices through which secondary metabolism in plants can be built in imaginative approaches to: 1) over-produce the valuable metabolites, 2) down-produce the poisonous metabolites, 3) produce the new metabolites. Secondary metabolites are extensively characterized as natural products integrated by a life form that is not basic to help development and life. The plant kingdom fabricates more than 200,000 unmistakable chemical compounds, a large portion of which emerge from particular metabolism. While these compounds assume critical jobs in interspecies challenge and safeguard, many plant natural products have been abused for use as prescriptions, scents, flavors, supplements, repellants, and colorants. In spite of this immense chemical decent variety, numerous secondary metabolites are available at low focuses in plant a, taking out yield based assembling as methods for achieving these imperative products. The basic and stereo chemical unpredictability of particular metabolites frustrates most endeavors to get to these compounds utilizing chemical blend. Albeit local plants can be built in amass target pathway metabolites. This Update gives a concise outline of designing plant secondary metabolism in microbial frameworks. We quickly diagram biosynthetic pathways intervening arrangement of the real classes of natural products with an accentuation on high-esteem terpenoids, alkaloids, phenylpropanoids, and polyketides. We additionally feature basic topics, techniques, and provoke hidden endeavors to reproduce and build these pathways in microbial hosts. We center mostly around again biosynthetic methodologies in which plant specific metabolites are combined straightforwardly from sugar feed stocks instead of enhanced forerunners or intermediates.

show abstract

Synthesis and biological evaluation of novel piperidine-benzodioxole derivatives designed as potential leishmanicidal drug candidates

Cited by 9 publications

References 23 publications

Chiral Amphiphilic Secondary Amine-Porphyrin Hybrids for Aqueous Organocatalysis

Chiral Amphiphilic Secondary Amine-Porphyrin Hybrids for Aqueous Organocatalysis

Drug Discovery for Cutaneous Leishmaniasis: A Review of Developments in the Past 15 Years

Chemistry of Secondary Metabolites

Contact Info

Product

Resources

About