Synthesis of Normorphans through an Efficient Intramolecular Carbamoylation of Ketones

Diaba, Fai͏̈za; Montiel, Juan A.; Şerban, Georgeta; Bonjoch, Josep

doi:10.1021/acs.orglett.5b01832

Cited by 17 publications

(16 citation statements)

References 46 publications

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“…It has been observed that the 2-amino-1,3,4-thiadiazole moiety may be a good group for anti-HIV-1 activity by providing promising antiviral agents. (7) substitution with F atoms (8,9) X = N heterocyclic ring increases activity introduction of CH 3 Although they exhibited less anti-HIV-1 activity compared to standard drug zidovudine (half-maximal inhibitory concentration IC 50 = 0.016 µM), these compounds showed significant anti-HIV-1 activity at micromolar concentrations (IC 50 within the range of 7.50-20.83 µM) ( Table 1). The introduction of electron-withdrawing groups, such as fluorine or trifluoromethyl on phenyl ring (derivatives 8 and 9), enhanced antiviral activity compared to the unsubstituted phenyl derivative 7.…”

Section: -10mentioning

confidence: 99%

“…It has been observed that the 2-amino-1,3,4-thiadiazole moiety may be a good group for anti-HIV-1 activity by providing promising antiviral agents. (7) substitution with F atoms (8,9) Molecular modeling studies for the pyrimidyl derivative 10 showed the formation of two potential intermolecular hydrogen bonds involving a nitrogen atom and the amino group of the thiadiazole ring and aminoacids from NNBS of RT. The introduction of electron-withdrawing groups, such as fluorine or trifluoromethyl on phenyl ring (derivatives 8 and 9), enhanced antiviral activity compared to the unsubstituted phenyl derivative 7.…”

Section: -10mentioning

confidence: 99%

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Viral infections have resulted in millions of victims in human history. [8][9][10][11][12][13][14]. There are currently approximately 90 drugs approved for the treatment of human viral infections.

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confidence: 99%

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Synthetic Compounds with 2-Amino-1,3,4-Thiadiazole Moiety Against Viral Infections

Şerban

2020

Molecules

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Viral infections have resulted in millions of victims in human history. Although great efforts have been made to find effective medication, there are still no drugs that truly cure viral infections. There are currently approximately 90 drugs approved for the treatment of human viral infections. As resistance toward available antiviral drugs has become a global threat to health, there is an intrinsic need to identify new scaffolds that are useful in discovering innovative, less toxic and highly active antiviral agents. 1,3,4-Thiadiazole derivatives have been extensively studied due to their pharmacological profile, physicochemical and pharmacokinetic properties. This review provides an overview of the various synthetic compounds containing the 2-amino-1,3,4-thiadiazole moiety that has been evaluated for antiviral activity against several viral strains and could be considered possible prototypes for the development of new antiviral drugs.Molecules 2020, 25, 942 2 of 22 due to the ability of viruses to undergo rapid mutations, the mechanisms involved in developing resistance to antiviral drugs are activated in most cases [1,3]. As resistance toward antiviral drugs is becoming a global health threat, there is an intrinsic need to identify new scaffolds that are useful in discovering innovative, less toxic and highly active antiviral agents [3,6,7]. Nitrogen-Containing Heterocycles and Thiadiazole Ring in Biology and Medicinal ChemistryNitrogen-containing heterocycles are widely distributed in nature and are essential in vegetal and animal metabolism. They are found in nucleic acids, vitamins, antibiotics, alkaloids, etc. [8][9][10][11][12][13][14]. In addition, nitrogen-containing heterocycles are important targets for medicinal chemistry, as they are found in more than half of the commercially available drugs and can also act as versatile intermediates in the synthesis of complex products that exhibit outstanding biological activities [15]. Most of the nitrogen-containing heterocyclic compounds exhibit better biological activity than non-nitrogen compounds [12,16,17]. Currently, there are approximately 90 drugs approved for use in the treatment of nine human viral infections caused by human immunodeficiency virus (HIV), hepatitis B virus (HBV), hepatitis C virus (HCV), herpes simplex virus (HSV), Influenza virus, human cytomegalovirus (HCMV), varicella-zoster virus (VZV), respiratory syncytial virus (RSV) and human papillomavirus [18]. Most of these drugs (e.g., acyclovir, cidofovir, idoxuridine, nevirapine, pleconaril, ribavirin, etc.) are nitrogen heterocycle molecules [3,19].Five-membered aromatic systems with three heteroatoms at symmetrical positions, such as the 1,3,4-thiadiazole ring, have been extensively studied due to their pharmacological profile and physicochemical and pharmacokinetic properties. 1,3,4-Thiadiazole derivatives are known as compounds having significant and diverse biological activities such as antibacterial, antifungal, antitubercular [20], analgesic and anti-inflammatory [21,22], antidepr...

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Section: -10mentioning

confidence: 99%

“…It has been observed that the 2-amino-1,3,4-thiadiazole moiety may be a good group for anti-HIV-1 activity by providing promising antiviral agents. (7) substitution with F atoms (8,9) Molecular modeling studies for the pyrimidyl derivative 10 showed the formation of two potential intermolecular hydrogen bonds involving a nitrogen atom and the amino group of the thiadiazole ring and aminoacids from NNBS of RT. The introduction of electron-withdrawing groups, such as fluorine or trifluoromethyl on phenyl ring (derivatives 8 and 9), enhanced antiviral activity compared to the unsubstituted phenyl derivative 7.…”

Section: -10mentioning

confidence: 99%

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Synthetic Compounds with 2-Amino-1,3,4-Thiadiazole Moiety Against Viral Infections

Şerban

2020

Molecules

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“…Nitrogen-containing heterocycles are found in a wide range of natural products and biologically active synthetic compounds (8)(9)(10)(11)(12)(13)(14)(15). In addition, nitrogen-containing heterocycles constitute a common structural unit of many marketed drugs (16,17).…”

Section: Pharmaceutical Chemistry Department Faculty Of Medicine Andmentioning

confidence: 99%

2-Amino-1,3,4-thiadiazoles as prospective agents in trypanosomiasis and other parasitoses

Şerban

2020

Acta Pharmaceutica

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Parasitic diseases are a serious public health problem affecting hundreds of millions of people worldwide. African trypanosomiasis, American trypanosomiasis, leishmaniasis, malaria and toxoplasmosis are the main parasitic infections caused by protozoan parasites with over one million deaths each year. Due to old medications and drug resistance worldwide, there is an urgent need for new antiparasitic drugs. 1,3,4-Thiadiazoles have been widely studied for medical applications. The chemical, physical and pharmacokinetic properties recommend 1,3,4-thiadiazole ring as a target in drug development. Many scientific papers report the antiparasitic potential of 2-amino-1,3,4-thiadiazoles. This review presents synthetic 2-amino-1,3,4-thiadiazoles exhibiting antitrypanosomal, antimalarial and antitoxoplasmal activities. Although there are insufficient results to state the quality of 2-amino-1,3,4-thiadiazoles as a new class of antiparasitic agents, many reported derivatives can be considered as lead compounds for drug synthesis and a promise for the future treatment of parasitosis and provide a valid strategy for the development of potent antiparasitic drugs.

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“…Lactic acid exists naturally in two optical isomers: d(-)-lactic acid and l(+)-lactic acid. Since elevated levels of the disomer are harmful to humans, l(+)-lactic acid is the preferred isomer for food-related and pharmaceutical industries [3,4]. It is the simplest 2-hydroxycarboxylic acid with a chiral atom and exists oin two enantiomeric firms (Fig.1).…”

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confidence: 99%

Study About HPLC Method Elaboration and Validation for Acid Lactic Assay in Grape Juice Fermentation Process

2019

Rev.Chim.

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In the present study, a simple and fast HPLC procedure has been developed for determination of a wide range of lactic acid concentrations. During the lactic acid analysis, the analytic column,YMC-Pack ODS AQ, was operating at 20oC. The mobile phase, 0.03% H3PO4:acetonitrile (88:12), was delivered isocratic, at a flow rate of 0.5 mL/min, in a 25 min run. The method was validate. The method could successfully used to quantify lactic acid in grape juice during fermentation. Keywords: Lactic acid, HPLC, grape juice

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Synthesis of Normorphans through an Efficient Intramolecular Carbamoylation of Ketones

Cited by 17 publications

References 46 publications

Synthetic Compounds with 2-Amino-1,3,4-Thiadiazole Moiety Against Viral Infections

Synthetic Compounds with 2-Amino-1,3,4-Thiadiazole Moiety Against Viral Infections

2-Amino-1,3,4-thiadiazoles as prospective agents in trypanosomiasis and other parasitoses

Study About HPLC Method Elaboration and Validation for Acid Lactic Assay in Grape Juice Fermentation Process

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