Ngampong Kongkathip

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In vitro and in silico studies of naphthoquinones and peptidomimetics toward Plasmodium falciparum plasmepsin V

Pichamon Sittikul, Napat Songtawee, Ngampong Kongkathip, Nonlawat Boonyalai

Biochimie > 2018 > 152 > C > 159-173

Plasmodium proteases play both regulatory and effector roles in essential biological processes in this important pathogen and have long been investigated as drug targets. Plasmepsin V from P. falciparum (PfPMV) is an essential protease that processes proteins for export into the host erythrocyte and is a focus of ongoing drug development efforts. In the present study, recombinant protein production,...

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An efficient synthesis and regioselective hydrogenolysis of dioxolane-type of carbohydrates

Boonsong Kongkathip, Nutthawat Chuanopparat, Ngampong Kongkathip

Tetrahedron > 2016 > 72 > 23 > 3296-3304

Carbohydrates, inexpensive chiral sources, are very useful for many syntheses of chiral bioactive compounds. We have chosen to synthesize benzyl α-d-mannofuranosides and d-lyxofuranosides with dioxolane-type, 2,3-O-isopentylidene and 2,3-O-benzylidene acetals from d-mannose. Interestingly, we have discovered new knowledge about the cleavage of dioxolane-type using two catalysts, Cu(OTf)₂/BH₃·THF and...

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A new and efficient asymmetric synthesis of oseltamivir phosphate (Tamiflu) from d-glucose

Boonsong Kongkathip, Sunisa Akkarasamiyo, Ngampong Kongkathip

Tetrahedron > 2015 > 71 > 16 > 2393-2399

The anti-influenza drug, oseltamivir phosphate (Tamiflu) was synthesized from d-glucose via a novel and efficient synthetic route. A unique feature of the synthesis is that the key intermediate aziridine cyclohexene was synthesized as a mixture of diastereomers, via a metal-mediated domino reaction and ring closing metathesis (RCM). The iodoxylose compound was prepared in 9 steps from d-glucose. Both...

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Biophysical and molecular docking studies of naphthoquinone derivatives on the ATPase domain of human Topoisomerase II

Nonlawat Boonyalai, Pichamon Sittikul, Narathip Pradidphol, Ngampong Kongkathip

Biomedicine & Pharmacotherapy > 2013 > 67 > 2 > 122-128

Numerous naphthoquinone derivatives, such as rhinacanthins function as anticancer drugs, which target hTopoII. The structure of hTopoII contains both an ATPase domain and a DNA binding domain. Several drugs bind to either one or both of these domains, thus modifying the activity of hTopoII. The naphthoquinone esters and amides used in this study showed that their hTopoIIα inhibitory activity was inversely...

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Synthesis of novel naphthoquinone aliphatic amides and esters and their anticancer evaluation

Boonsong Kongkathip, Sunisa Akkarasamiyo, Komkrit Hasitapan, Pichamon Sittikul, more

European Journal of Medicinal Chemistry > 2013 > 60 > C > 271-284

Fourteen new naphthoquinone aliphatic amides and seventeen naphthoquinone aliphatic esters were synthesized in nine to ten steps from 1-hydroxy-2-naphthoic acid with 9–25% overall yield for the amides, and 16–21% overall yield for the esters. The key step of the amide synthesis is a coupling reaction between amine and various aliphatic acids using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium...

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A new and efficient asymmetric synthesis of oseltamivir phosphate (Tamiflu) from d-mannose

Nutthawat Chuanopparat, Ngampong Kongkathip, Boonsong Kongkathip

Tetrahedron Letters > 2012 > 53 > 46 > 6209-6211

Oseltamivir phosphate (Tamiflu) was synthesized from d-mannose through a short and practical synthetic route. A unique feature of the route is that the bulky 3-pentyloxy group and adjacent acetamide of Tamiflu were introduced at an early stage of the synthesis by copper-catalyzed regioselective ring-opening of the 2,3-pentylidene ketal of d-lyxofuranoside. The d-lyxofuranoside ethylphosphonate precursor...

article

A concise and practical synthesis of oseltamivir phosphate(Tamiflu) from d-mannose

Nutthawat Chuanopparat, Ngampong Kongkathip, Boonsong Kongkathip

Tetrahedron > 2012 > 68 > 34 > 6803-6809

A short and practical synthesis of oseltamivir phosphate was accomplished in 11 steps from inexpensive and abundant starting material, d-mannose. This synthetic route featured an intramolecular Horner–Wadsworth–Emmons reaction as the key step to furnish the cyclohexene ring product. The hydroxyl group was converted stereo specifically into an amino group by oxidation to the ketone and reductive amination...

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First synthesis and anticancer activity of novel naphthoquinone amides

Narathip Pradidphol, Ngampong Kongkathip, Pichamon Sittikul, Nonlawat Boonyalai, more

European Journal of Medicinal Chemistry > 2012 > 49 > Complete > 253-270

Sixteen novel naphthoquinone aromatic amides were synthesized by a new route starting from 1-hydroxy-2-naphthoic acid in nine or ten steps with good to excellent yield. Amide formation reaction was carried out by using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) as an efficient condensing agent leading to carboxamides in high yield. The key step for converting naphthol...

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Regioselective ring opening of exo- and endo-3,4-benzylidene acetals of arabinopyranoside derivatives with Lewis acids and reducing agents

Janjira Rujirawanich, Boonsong Kongkathip, Ngampong Kongkathip

Carbohydrate Research > 2011 > 346 > 7 > 927-932

Dioxolane type 3,4-benzylidene acetals of benzyl β-l-arabinose either as a mixture or pure exo- and endo-isomers cleavaged with BF ₃ ·OEt ₂ /Et ₃ SiH in dichloromethane or acetonitrile regioselectively, provided the 4-O-benzyl-3-hydroxy derivative. The reaction with TiCl ₄ /Et ₃ SiH or Cu(OTf) ₂ /Et ₃ SiH provided a mixture of 3- and 4-O-benzyl...

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Synthesis of cytotoxic novel 9,11-secosterol analogs: Structure/activity studies

Boonsong Kongkathip, Anuch Hasakunpaisarn, Suthinee Boonananwong, Ngampong Kongkathip

Steroids > 2010 > 75 > 12 > 834-847

In an effort to determine the pharmaceutical utility and the structural requirements for activity against tumor cell lines, 30 novel 9,11-secosterol analogues with different side chains and degrees of oxidation at C-9 were synthesized starting from hecogenin. Evaluation of the synthesized compounds for cytotoxicity against KB, HeLa and MCF-7 cell lines revealed that some important structural features...

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An efficient synthesis of oseltamivir phosphate (Tamiflu) via a metal-mediated domino reaction and ring-closing metathesis

Pawinee Wichienukul, Sunisa Akkarasamiyo, Ngampong Kongkathip, Boonsong Kongkathip

Tetrahedron Letters > 2010 > 51 > 24 > 3208-3210

An efficient synthesis of the influenza neuraminidase inhibitor prodrug oseltamivir phosphate (Tamiflu) from cheap, commercially available d-ribose is described. The main features of this approach comprise a metal (Zn, In)-mediated domino reaction and ring-closing olefin metathesis (RCM) of the resultant functionalized dienes to produce the Tamiflu skeleton. The synthesis described in this Letter...

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Further study on synthesis and evaluation of 3,16,20-polyoxygenated steroids of marine origin and their analogs as potent cytotoxic agents

Potjamarn Bunyathaworn, Suthinee Boonananwong, Boonsong Kongkathip, Ngampong Kongkathip

Steroids > 2010 > 75 > 6 > 432-444

A series of new polyoxygenated steroid derivatives with various steroid skeleton moieties were synthesized. Antitumor activity of the compounds against three tumor cell lines (Breast cancer MCF7, lung cancer NCI and oral cancer KB) were evaluated. Compounds with aromatic A ring of this series exhibited the most potent cytotoxicities in all tested cells. The absence of OH at C-16 or lack of cholesterol...

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Transforming Rhinacanthin Analogues from Potent Anticancer Agents into Potent Antimalarial Agents

Ngampong Kongkathip, Narathip Pradidphol, Komkrit Hasitapan, Ronald Grigg, more

Journal of Medicinal Chemistry > 2010 > 53 > 3 > 1211 - 1221

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First synthesis of 3,16,20-polyoxygenated cholestanes, new cytotoxic steroids from the gorgonian Leptogorgia sarmentosa

Suthinee Boonananwong, Boonsong Kongkathip, Ngampong Kongkathip

Steroids > 2008 > 73 > 11 > 1123-1127

Using tigogenin as starting material, (20S)-20-hydroxycholestane-3,6-dione (1), (16S, 20S)-16,20-dihydroxycholestan-3-one (2), (20S)-20-hydroxycholest-1-ene-3,16-dione (3) and (20S)-20-hydroxycholest-4-ene-3,16-dione (4), natural polyoxygenated steroids from the gorgonian, Leptogorgia sarmentosa, were synthesized in four steps. Antitumor activity against three tumor cell lines (breast cancer, MCF7,...

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Novel laccases of Ganoderma sp. KU-Alk4, regulated by different glucose concentration in alkaline media

Churapa Teerapatsakul, Naoki Abe, Christopher Bucke, Ngampong Kongkathip, more

World Journal of Microbiology and Biotechnology > 2007 > 23 > 11 > 1559-1567

Physiological regulation of laccase production from Ganoderma sp. KU-Alk4, isolated in Thailand, was controlled by the initial glucose concentration in liquid culture. Different laccase isozymes were produced using different starting concentrations of glucose. With 1% glucose, two isozymes, KULac 1 and 2 were produced, while with 4% glucose, three different isozymes, KULac 3, 4 and 5, were produced...

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Catalytic processes for the functionalisation and desymmetrisation of malononitrile derivatives

Ronald Grigg, Anuch Hasakunpaisarn, Colin Kilner, Boonsong Kongkathip, more

Tetrahedron > 2005 > 61 > 39 > 9356-9367

Palladium catalysed 3-component cascades are described involving aryl/heteroaryl iodides, allene and benzyl malononitrile. Catalytic monohydration and monoamination of malononitriles to the corresponding monoamides and monoamidines are also described together with several examples of mono-oxazoline formation.

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Inhibitory effects of 2-substituted-1-naphthol derivatives on cyclooxygenase I and II

Boonsong Kongkathip, Chak Sangma, Kanyawim Kirtikara, Suwaporn Luangkamin, more

Bioorganic & Medicinal Chemistry > 2005 > 13 > 6 > 2167-2175

Naphthol derivatives, 2-(3′-hydroxypropyl)-naphthalen-1-ol (2), 2-(3′-hydroxy-2′-methylpropyl)-naphthalen-1-ol (3) and 2-(3′-hydroxy-2′,2′-dimethylpropyl)-naphthalen-1-ol (7) were synthesized and already reported by our group. Therefore in this paper we described further synthesis of their ether derivatives, 3-(1-methoxy-naphthalen-2-yl)-propan-1-ol (4), 3-(1-methoxy-naphthalen-2-yl)-2methyl-propan-1-ol...

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Biologically active substances from amphibians: preliminary studies on anurans from twenty-one genera of Thailand

John W. Daly, Naratitt Noimai, Boonsong Kongkathip, Ngampong Kongkathip, more

Toxicon > 2004 > 44 > 8 > 805-815

Amphibian skin has been the source of a wide variety of biologically active substances, but less than one-third of the known genera of amphibians have been probed for such active substances. Skins of 21 genera of anurans from Thailand have now been investigated for noxious secretions, toxic substances, and alkaloids. Four genera of bufonid toads (Bufo, Ansonia, Leptophryne, Pedostipes) were toxic...

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Synthesis of Novel Rhinacanthins and Related Anticancer Naphthoquinone Esters

Ngampong Kongkathip, Suwaporn Luangkamin, Boonsong Kongkathip, Chak Sangma, more

Journal of Medicinal Chemistry > 2004 > 47 > 18 > 4427 - 4438

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Potent antitumor activity of synthetic 1,2-Naphthoquinones and 1,4-Naphthoquinones

Ngampong Kongkathip, Boonsong Kongkathip, Pongpun Siripong, Chak Sangma, more

Bioorganic & Medicinal Chemistry > 2003 > 11 > 14 > 3179-3191

Rhinacanthone (1) and two 1,2-pyranonaphthoquinones (2,3) were synthesized and found to show very potent cytotoxicity against three cancer cell lines (KB, HeLa and HepG ₂ ) with IC ₅ ₀ values of 0.92-9.63μM, whereas the corresponding hydroxylated derivative 4 had reduced cytotoxicity (IC ₅ ₀ values of 7.61-24.13μM). Three 1,2-furanonaphthoquinone derivatives (5-7) were...

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Search results for: Ngampong Kongkathip

In vitro and in silico studies of naphthoquinones and peptidomimetics toward Plasmodium falciparum plasmepsin V

An efficient synthesis and regioselective hydrogenolysis of dioxolane-type of carbohydrates

A new and efficient asymmetric synthesis of oseltamivir phosphate (Tamiflu) from d-glucose

Biophysical and molecular docking studies of naphthoquinone derivatives on the ATPase domain of human Topoisomerase II

Synthesis of novel naphthoquinone aliphatic amides and esters and their anticancer evaluation

A new and efficient asymmetric synthesis of oseltamivir phosphate (Tamiflu) from d-mannose

A concise and practical synthesis of oseltamivir phosphate(Tamiflu) from d-mannose

First synthesis and anticancer activity of novel naphthoquinone amides

Regioselective ring opening of exo- and endo-3,4-benzylidene acetals of arabinopyranoside derivatives with Lewis acids and reducing agents

Synthesis of cytotoxic novel 9,11-secosterol analogs: Structure/activity studies

An efficient synthesis of oseltamivir phosphate (Tamiflu) via a metal-mediated domino reaction and ring-closing metathesis

Further study on synthesis and evaluation of 3,16,20-polyoxygenated steroids of marine origin and their analogs as potent cytotoxic agents

Transforming Rhinacanthin Analogues from Potent Anticancer Agents into Potent Antimalarial Agents

First synthesis of 3,16,20-polyoxygenated cholestanes, new cytotoxic steroids from the gorgonian Leptogorgia sarmentosa

Novel laccases of Ganoderma sp. KU-Alk4, regulated by different glucose concentration in alkaline media

Catalytic processes for the functionalisation and desymmetrisation of malononitrile derivatives

Inhibitory effects of 2-substituted-1-naphthol derivatives on cyclooxygenase I and II

Biologically active substances from amphibians: preliminary studies on anurans from twenty-one genera of Thailand

Synthesis of Novel Rhinacanthins and Related Anticancer Naphthoquinone Esters

Potent antitumor activity of synthetic 1,2-Naphthoquinones and 1,4-Naphthoquinones

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