Synthesis, thermal stability, antimalarial activity of symmetrically and asymmetrically substituted tetraoxanes

Atheaya, Himanshu; Khan, Shabana I.; Mamgain, Ritu; Rawat, Diwan S.

doi:10.1016/j.bmcl.2007.12.069

Cited by 50 publications

(22 citation statements)

References 41 publications

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“…With this objective, we prepared asymmetrical tetraoxanes by oxidative coupling of bishydroperoxides in the presence of H 2 O 2 /2,2,2-trifluoroethanol (TFE) in the presence of MeReO 3 as a catalyst (Schemes 4 and 5). 54 Antimalarial activity evaluation of these compounds revealed that asymmetrical tetraoxanes with cyclopentyl or cycloheptyl groups (46a-46c, 46i-46k) exhibit poor antimalarial activity against D6 (IC 50 ranging from 3.81 to 14.60 mM) and W2 (IC 50 ranging from 1.82 to 18.54 mM) clones of P. falciparum with low selectivity. 54 Interestingly, symmetrically substituted tetraoxanes with methyl substituents (47a-47c) exhibit good antimalarial activity against D6…”

Section: R E T R a C T E Dmentioning

confidence: 99%

“…However, substitution of CH 3 by CF 3 results in total loss of antimalarial activity (entry 47k and 47l). 54 Solid-state thermal stability of these compounds have also been studied by differential scanning calorimetry and it was found that symmetrically substituted tetraoxanes have better thermal stability than their asymmetric tetraoxane counter parts. 54 Activity profile of this series of compounds revealed that tolyl-based tetraoxanes exhibit (47a-47c) better antimalarial activity than other compounds of the series, so it was worth to synthesize alkylsubstituted tetraoxanes so that SAR can be carried out.…”

Section: R E T R a C T E Dmentioning

confidence: 99%

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Tetraoxanes: Synthetic and Medicinal Chemistry Perspective

Kumar¹,

Savan²,

Rawat

2010

Medicinal Research Reviews

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The discovery of artemisinin from Chinese medicinal plant, Artemisia annua in 1971, opened a new era in the malarial chemotherapy. This discovery was the beginning of exploring peroxides as potential replacements for the traditional antimalarial drugs such as chloroquine and mefloquine. The structurally simple class of peroxides that emerged from these studies was the 1,2,4,5-tetraoxanes. This study describes the current status of tetraoxane-based antimalarials that show significant promises because of their artemisinin-like activity. Literature from 1999 has been critically reviewed and an attempt has been made to discuss various synthetic methods and structure-activity relationship study among the series of tetraoxane-based compounds. © 2010 Wiley Periodicals, Inc. Med Res Rev.

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Section: R E T R a C T E Dmentioning

confidence: 99%

Section: R E T R a C T E Dmentioning

confidence: 99%

Tetraoxanes: Synthetic and Medicinal Chemistry Perspective

Kumar¹,

Savan²,

Rawat

2010

Medicinal Research Reviews

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“…The previous studies from our laboratory (32,33) and others showed that aminoquinoline-triazine hybrids exhibit potent antimalarial activity (37,38). In continuation to our efforts towards the development of new antimalarials (39)(40)(41)(42), we report herein synthesis and antimalarial activity of…”

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confidence: 77%

“…The previous studies from our laboratory and others showed that aminoquinoline‐triazine hybrids exhibit potent antimalarial activity . In continuation to our efforts towards the development of new antimalarials , we report herein synthesis and antimalarial activity of series of new 4‐aminoquinoline‐triazine‐based hybrids. Systematic chemical modification in the triazine ring and linker led to the discovery of many potent antimalarial agents.…”

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confidence: 82%

4‐Aminoquinoline‐Triazine‐Based Hybrids with Improved In Vitro Antimalarial Activity Against CQ‐Sensitive and CQ‐Resistant Strains of Plasmodium falciparum

2013

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A systematic chemical modification in the triazine moiety covalently attached via suitable linkers to 4-amino-7-chloroquinolines yielded a series of new 7-chloro-4-aminoquinoline-triazine hybrids exhibiting high in vitro activity against W2 (chloroquine-resistant) and D6 (chloroquine-sensitive) strains of Plasmodium falciparum without any toxicity against mammalian cell lines (Vero, LLC-PK11, HepG2). Many of the compounds (6, 8, 10, 11, 13, 14, 16, 27, 29 and 33) showed excellent potency against chloroquine sensitive and resistant strains. In particular, compounds 6, 8, 14, 16 and 29 were found to be significantly more active than chloroquine against the chloroquine-resistant strains (W2 clone) of P. falciparum.

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“…The use of the 30% Н 2 О 2 /MeReO 3 (МТО)/fluorinated alcohol system enabled the synthesis of symmetrical compounds 392 from aldehydes 391 and unsymmetrical tetraoxanes 393 containing aryl (peroxide-destabilizing) substituents from aldehydes 391 (and cycloalkanones) (Scheme 119) [422]. …”

Section: Reviewmentioning

confidence: 99%

Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products

Terent’ev¹,

Borisov²,

Vil³

et al. 2014

Beilstein J. Org. Chem.

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SummaryThe present review describes the current status of synthetic five and six-membered cyclic peroxides such as 1,2-dioxolanes, 1,2,4-trioxolanes (ozonides), 1,2-dioxanes, 1,2-dioxenes, 1,2,4-trioxanes, and 1,2,4,5-tetraoxanes. The literature from 2000 onwards is surveyed to provide an update on synthesis of cyclic peroxides. The indicated period of time is, on the whole, characterized by the development of new efficient and scale-up methods for the preparation of these cyclic compounds. It was shown that cyclic peroxides remain unchanged throughout the course of a wide range of fundamental organic reactions. Due to these properties, the molecular structures can be greatly modified to give peroxide ring-retaining products. The chemistry of cyclic peroxides has attracted considerable attention, because these compounds are used in medicine for the design of antimalarial, antihelminthic, and antitumor agents.

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Synthesis, thermal stability, antimalarial activity of symmetrically and asymmetrically substituted tetraoxanes

Cited by 50 publications

References 41 publications

Tetraoxanes: Synthetic and Medicinal Chemistry Perspective

Tetraoxanes: Synthetic and Medicinal Chemistry Perspective

4‐Aminoquinoline‐Triazine‐Based Hybrids with Improved In Vitro Antimalarial Activity Against CQ‐Sensitive and CQ‐Resistant Strains of Plasmodium falciparum

Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products

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