Tanatorn Khotavivattana

Chulalongkorn University · Department of Chemistry

The prevalence of HIV-1 infection continues to pose a significant global public health issue, highlighting the need for antiretroviral drugs that target viral proteins to reduce viral replication. One such target is HIV-1 protease (PR), responsible for cleaving viral polyproteins, leading to the maturation of viral proteins. While darunavir (DRV) i...

In the pursuit of novel antiretroviral therapies for human immunodeficiency virus type‐1 (HIV‐1) proteases (PRs), recent improvements in drug discovery have embraced machine learning (ML) techniques to guide the design process. This study employs ensemble learning models to identify crucial substructures as significant features for drug development...

Chikungunya virus is a re-emerging arbovirus that has caused epidemic outbreaks in recent decades. Patients in older age groups with high viral load and severe immunologic response during acute infection are likely to develop chronic arthritis and severe joint pain. Currently, no antiviral drug is available. Previous studies suggested that a flavon...

A mild electrochemical oxidative cyclization for the synthesis of flavones from easy‐access 2’‐hydroxychalcones was developed using an inexpensive NaI as mediator and electrolyte under ambient temperature in a mixture of EtOH and H2O as solvent. This method was successfully applied to synthesize 26 examples of flavones from a variety of functionali...

Flavone has recently been proved as a promising scaffold for the development of a novel drug against dengue fever, one of the major health threats globally. However, the structure–activity relationship study of flavones on the anti-dengue activity remains mostly limited to the natural-occuring analogs. Herein, 27 flavone analogs were successfully s...

Psoralen derivatives are well known for their unique phototoxicity and also exhibits promising anti-breast cancer activity both in the presence and the absence of UVA irradiation. However, the structure–activity relationship on this scaffold remains lacking. Herein, a series of psoralen derivatives with various C-5 substituents were synthesized and...

In the fight towards eradication of malaria, identifying compounds active against new drug targets constitutes a key approach. Plasmodium falciparum 7,8-dihydro-6-hydroxymethylpterin-pyrophosphokinase (PfHPPK) has been advanced as a promising target, as being part of the parasite essential folate biosynthesis pathway while having no orthologue in t...

Psoralen derivatives are well known for their unique phototoxicity and also exhibited promising anti-breast cancer activity both in the presence and the absence of UVA irradiation. However, the structure-activity relationship on this scaffold remains lacking. Herein, a series of psoralen derivatives with various C-5 substituents were synthesized an...

A flavonoid is a versatile core structure with various cellular, immunological, and pharmacological effects. Recently, flavones have shown anti-dengue activities by interfering with viral translation and replication. However, the molecular target is still elusive. Here we chemically modified apigenin by adding an alkyne moiety into the B-ring hydro...

The rapid emergence of drug resistance to the current antimalarial agents has led to the urgent need for the discovery of new and effective compounds. In this work, a series of 5-phenoxy primaquine analogs with 8-aminoquinoline core (7a–7h) was synthesized and investigated for their antimalarial activity against Plasmodium falciparum. Most analogs...

Twelve derivatives of biguanide-derived 1,3,5-triazines, a promising class of anticancer agent, were synthesised and evaluated for their anticancer activity against two colorectal cancer cell lines—HCT116 and SW620. 2c and 3c which are the derivatives containing o-hydroxyphenyl substituents exhibited the highest activity with IC50 against both cell...

Alkyl quinolone has been proven to be a privileged scaffold in the antimicrobial drug discovery pipeline. In this study, a series of new 4-hydroxy-2-quinolinone analogs containing a long alkyl side chain at C-3 and a broad range of substituents on the C-6 and C-7 positions were synthesized. The antibacterial and antifungal activities of these analo...

Bioassay‐guided fractionation was conducted on dichloromethane extract from the rhizomes of Globba schomburgkii Hook.f. which have previously been reported as the part with the highest antibacterial activity. 10 fractions and 20 sub‐fractions were obtained and evaluated for their potency against various strains of bacteria. The most active sub‐frac...

In this work, the preparation of novel calcium citrate (CaCit) nanoparticles (NPs) has been disclosed and the use of these NPs as “Trojan” carriers has been demonstrated. The concentration ratio between calcium ions and citrate ions was optimized, yielding spherical NPs with size in the range of 100–200 nm. Additionally, a fluorescent dye, fluoresc...

Cover Picture. Globba schomburgkii Hook.f. (Zingiberaceae) or ‘dancing girl ginger' is an ornamental plant largely found in tropical Asia, especially in the Saraburi Province of Thailand where it is used in religious ceremonies during the Buddhist Lent. To investigate the further applications of the plant, twelve crude extracts from rhizomes, stalk...

Background Although the levels of intact parathyroid hormone (iPTH) are well‐controlled following the KDIGO guideline, the incidence of osteoporosis and fracture are still high in hemodialysis (HD) patients. This study was conducted to investigate the correlation between bone turnover markers, bone mineral density (BMD), and bone histomorphometry i...

Peroxy-functionalized magnetic mesoporous silica (MMS-PA) composites containing magnetic nanoparticles (MNPs) and peroxy acids were synthesized to be used as an easily reusable heterogeneous oxidant for the epoxidation of alkenes. The presence of peroxy acid functional groups on the composites was confirmed by Fourier transform infrared spectroscop...

A series of melodorinol analogues were synthesized via a diverted total synthesis approach, leading to structural modifications on several regions of the molecule. Their cytotoxicity was evaluated against five human cancer cell lines (KB, HeLa-S3, MCF-7, HT-29 and A549). Structure-activity relationship studies revealed key parameters that affect th...

The 18F-labeling of 5-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate, commonly referred to as the Umemoto reagent, has been accomplished applying a halogen exchange 18F-fluorination with 18F-fluoride, followed by oxidative cyclization with Oxone® and trifluoromethanesulfonic anhydride. This new 18F-reagent allows for the direct chemo...

In this work, we describe the (18)F-labeling of α,α-difluoro-α-(aryloxy)acetic acid derivatives and demonstrate that these building blocks are amenable to post-(18)F-fluorination functionalization. Protodecarboxylation offers a new entry to (18)F-difluoromethoxyarene, and the value of this approach is further demonstrated with coupling processes le...

Alkenes substituted with a thiourea undergo C–CF 3 followed by intramolecular C–S bond formation with the Togni reagent and trifluoroacetic acid (TFA) at room temperature; thiols and thioamides are not suitable S-sources for this reaction. This anti-addition process involves a CF 3 radical, and affords CF 3-substituted thiazolines and thiazines for...

We report the synthesis of [F-18]arylCF(3) and [F-18]arylCHF(2) derivatives from arylCF(2)Br and arylCHFCl precursors applying a silver-mediated halogen exchange with [F-18]fluoride. In the absence of Ag(I)OTf, no reaction takes place at room temperature for both classes of substrates; this result demonstrates the beneficial role of silver(I) as a...

We report that halogenophilic silver(I) triflate permits halogen exchange (halex) nucleophilic (18) F-fluorination of aryl-OCHFCl, -OCF2 Br and -SCF2 Br precursors under mild conditions. This Ag(I) -mediated process allows for the first time access to a range of (18) F-labeled aryl-OCHF2 , -OCF3 and -SCF3 derivatives, inclusive of [(18) F]riluzole....

We report that halogenophilic silver(I) triflate permits halogen exchange (halex) nucleophilic 18F-fluorination of aryl-OCHFCl, -OCF2Br and -SCF2Br precursors under mild conditions. This AgI-mediated process allows for the first time access to a range of 18F-labeled aryl-OCHF2, -OCF3 and -SCF3 derivatives, inclusive of [18F]riluzole. The 18F-labeli...

A visible light-mediated hydrotrifluoromethylation of unactivated alkenes is disclosed using the Umemoto reagent as the CF3 source and MeOH as the reductant. This effective transformation operates at room temperature in the presence of 5 mol% Ru(bpy)3Cl2; the process is characterized by its operational simplicity and functional group tolerance.

This paper describes a new catalytic method for the regio- and stereocontrolled fluorination of allylic carbonates. This transformation uses TBAF·4tBuOH as the fluoride source and [Ir(COD)Cl]2 as the catalyst; the most commonly used [Ir(COD)Cl]2/phosphoramidite system is ineffective. Synthetically, this reaction is characterized by a high degree of...