Evaluation of Some Pyrazoloquinolines as Inhibitors of Herpes Simplex Virus Type 1 Replication

Bekhit, Adnan A.; El-Sayed, Ola A.; Aboul‐Enein, Hassan Y.; Siddiqui, Yunus M.; Al‐Ahdal, Mohammed N.

doi:10.1002/ardp.200400930

Cited by 12 publications

(11 citation statements)

References 34 publications

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“…Keeping this in mind, we synthesized several pharmacologically active aminopyrazoloquinoline derivatives with and without sugar moieties, which have been shown to possess different degree of antiviral activities against HSV-type 1 (HSV-1) (1, 2). The 3-amino-7-methoxy-1H-pyrazolo [3, 4-b] quinoline (compound 3, Fig.…”

Section: Introductionmentioning

confidence: 99%

“…Acyclovir had been the drug of choice for several decades; however, the emergence of acyclovir-resistant Herpes Simplex Virus (HSV) isolate in the immunocompromised patients and organ or bone marrow recipients has led to the discovery of new antiviral compounds ( 3 - 5 , 9 , 10 ). Keeping this in mind, we synthesized several pharmacologically active aminopyrazoloquinoline derivatives with and without sugar moieties, which have been shown to possess different degree of antiviral activities against HSV-type 1 (HSV-1) ( 1 , 2 ). The 3-amino-7-methoxy-1H-pyrazolo [3, 4-b] quinoline (compound 3, Fig.…”

Section: Introductionmentioning

confidence: 99%

“…The 3-amino-7-methoxy-1H-pyrazolo [3, 4-b] quinoline (compound 3, Fig. 1 ) was found to be equally effective antiviral compound as acyclovir at equimolar basis ( 2 ). Although aldehydo-sugar derivatives of pyrazoloquinoline (compounds 4 and 5, Fig.…”

Section: Introductionmentioning

confidence: 99%

“…Although aldehydo-sugar derivatives of pyrazoloquinoline (compounds 4 and 5, Fig. 1 ) inhibited the HSV-1 replication, their precursors were more effective anti-HSV-1 ( 2 ).…”

Section: Introductionmentioning

confidence: 99%

“…Apoptosis is a well-established and recognized biomarker to screen the new compounds for cytotoxicity ( 6 , 11 - 13 ). On the basis of our published report ( 2 ) regarding the antiviral activities of these aminopyrazoloquinoline precursors and their aldehydo-sugar derivatives, we selected only the most effective antiviral derivatives for evaluation of cytotoxic potential.…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxic and genotoxic potentials of newly synthesized antiviral aminopyrazoloquinoline derivatives

et al. 2007

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In the present study, we screened newly synthesized antiviral aminopyrazoloquinoline derivatives for their cytotoxic and genotoxic potential in human normal and breast cancer cell lines using apoptosis and DNA adducts biomarkers. The compounds, along with the well-known antiviral drug acyclovir, were incubated with the normal (MCF-10A, MCF-12A) and cancer (MCF-7, MDA-MB-231) cell lines at 10, 50, and 100 lM for 72 h at 37°C. The most potent antiviral methoxy derivative (compound 3) was found to be more cytotoxic in the normal breast epithelial cell lines (MCF-10A and MCF-12A) and MDA-MB-231 cell lines at 50 lM. MCF-7 cells were found to be almost completely resistant to all these compounds while MDA-MB-231 cell lines were significantly killed by apoptosis. Acyclovir was ineffective in all these cell lines. We further tested these compounds using modulation of benzo[a]pyrene (BP)-DNA adduct formation in these cell lines. An inverse correlation was found between the degree of apoptosis and BP-DNA adduct levels for most of these compounds, although this seems to be the case only with the cancer cell lines. Our results suggest that the newly synthesized antiviral compounds have an associated risk of cytotoxicity and/or genotoxicity compared to acyclovir.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Although aldehydo-sugar derivatives of pyrazoloquinoline (compounds 4 and 5, Fig. 1 ) inhibited the HSV-1 replication, their precursors were more effective anti-HSV-1 ( 2 ).…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cytotoxic and genotoxic potentials of newly synthesized antiviral aminopyrazoloquinoline derivatives

et al. 2007

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Effect of Pyrazoloquinoline Derivatives on the Growth of Leishmania donovani Promastigotes

Al‐Qahtani

Siddiqui

Bekhit

et al. 2005

Archiv der Pharmazie

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A screening study was conducted to examine the effect of a series of synthesized pyrazoloquinoline derivatives on the growth of Leishmania donovani promastigotes. Sixteen compounds were tested, ten of which showed an inhibitory effect on the growth of promastigotes. Compound 1 demonstrated potent antileishmanial activity, followed by compounds 3 and 7. Some compounds showed less significant activities, while others exhibited little or no activity. Some of these compounds may be potential candidates for future treatment of leishmaniasis.

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Electrocatalytic Multicomponent Transformation of Aldehyde, 5‐Amino‐3‐methyl‐1‐phenylpyrazole and Dimedone: An Efficient Protocol for Substituted Pyrazolo[3,4‐b]quinolines

Qian

Wang

et al. 2023

ChemistrySelect

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A convenient, rapid and electrochemical one‐pot protocol was developed successfully for the preparation of pyrazolo[3,4‐b]‐quinoline derivatives. The reaction is carried out in a 25 mL three neck flask equipped with graphite electrode as anode and iron electrode as cathode (electrode area of 1 cm2) with sodium bromide as supporting electrolyte at room temperature in ethanol. Fourteen pyrazolo‐[3,4‐b]‐quinoline derivatives were synthesized by use of various aldehyde (including aryl aldehydes and aliphatic aldehydes), dimedone and 5‐amino‐3‐methyl‐1‐phenylpyrazole as substrates in good yields (76–86 %) with a constant current of 30 mA after 0.14 F/mol of electricity passed. All aimed products were characterized by IR, 1H NMR and HRMS. Notably, the presented method features ecologically sound, simple experimental procedure and good yields.

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Evaluation of Some Pyrazoloquinolines as Inhibitors of Herpes Simplex Virus Type 1 Replication

Cited by 12 publications

References 34 publications

Cytotoxic and genotoxic potentials of newly synthesized antiviral aminopyrazoloquinoline derivatives

Cytotoxic and genotoxic potentials of newly synthesized antiviral aminopyrazoloquinoline derivatives

Effect of Pyrazoloquinoline Derivatives on the Growth of Leishmania donovani Promastigotes

Electrocatalytic Multicomponent Transformation of Aldehyde, 5‐Amino‐3‐methyl‐1‐phenylpyrazole and Dimedone: An Efficient Protocol for Substituted Pyrazolo[3,4‐b]quinolines

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