1076-56-8Relevant articles and documents
Reaction of natural-occurring phenolic derivatives with bis(trimethylsilyl) sulfate
Nuissier,Bourgeois,Grignon-Dubois
, p. 506 - 507 (2008)
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Alkylphenol activity against candida spp. and microsporum canis: A focus on the antifungal activity of thymol, eugenol and o-methyl derivatives
Fontenelle, Raquel O.S.,Morais, Selene M.,Brito, Erika H.S.,Brilhante, Raimunda S.N.,Cordeiro, Rossana A.,Lima, Ynayara C.,Brasil, Nilce V.G.P.S.,Monteiro, Andre J.,Sidrim, Jose J.C.,Rocha, Marcos F.G.
, p. 6422 - 6431 (2011)
In recent years there has been an increasing search for new antifungal compounds due to the side effects of conventional antifungal drugs and fungal resistance. The aims of this study were to test in vitro the activity of thymol, eugenol, estragole and anethole and some O-methyl-derivatives (methylthymol and methyleugenol) against Candida spp. and Microsporum canis. The broth microdilution method was used to determine the minimum inhibitory concentration (MIC). The minimum fungicidal concentrations (MFC) for both Candida spp. and M. canis were found by subculturing each fungal suspension on potato dextrose agar. Thymol, methylthymol, eugenol, methyleugenol, anethole, estragole and griseofulvin respectively, presented the following MIC values against M. canis: 4.8-9.7; 78-150; 39; 78-150; 78-150; 19-39 μg/mL and 0.006-2.5 μg/mL. The MFC values for all compounds ranged from 9.7 to 31 μg/mL. Concerning Candida spp, thymol, methylthymol, eugenol, methyleugenol, anethole, estragole and amphotericin, respectively, showed the following MIC values: 39; 620-1250; 150-620; 310-620; 620; 620-1250 and 0.25-2.0 μg/mL. The MFC values varied from 78 to 2500 μg/mL. All tested compounds thus showed in vitro antifungal activity against Candida spp. and M. canis. Therefore, further studies should be carried out to confirm the usefulness of these alkylphenols in vivo.
Identification and structure-activity relationship study of carvacrol derivatives as Mycobacterium tuberculosis chorismate mutase inhibitors
Alokam, Reshma,Jeankumar, Variam Ullas,Sridevi, Jonnalagadda Padma,Matikonda, Siddharth Sai,Peddi, Santosh,Alvala, Mallika,Yogeeswari, Perumal,Sriram, Dharmarajan
, p. 547 - 554 (2014)
In the present study, we identified carvacrol, a major phenolic component of oregano oil as a novel small molecule inhibitor of Mycobacterium tuberculosis (MTB) chorismate mutase (CM) enzyme with IC50 of 1.06±0.4μM. Virtual screening of the BITS-Pilani in-house database using the crystal structure of the MTB CM bound transition state intermediate (PDB: 2FP2) as framework identified carvacrol as a potential lead. Further various carvacrol derivatives were evaluated in vitro for their ability to inhibit MTB CM enzyme, whole cell MTB and cytotoxicity as steps toward the derivation of structure-activity relationships (SAR) and lead optimization.
Antioxidant and tyrosinase docking studies of heterocyclic sulfide derivatives containing a thymol moiety
Havasi, Mia H.,Ressler, Andrew J.,Parks, Eden L.,Cocolas, Alexander H.,Weaver, Ashton,Seeram, Navindra P.,Henry, Geneive E.
, (2020/02/26)
Fourteen heterocyclic sulfide derivatives (4–17) containing a thymol moiety and oxadiazole, thiadiazole, triazole, oxazole, thiazole, imidazole, pyridine or purine heterocycles were synthesized in three steps. The cupric, Cu(II), ion reducing antioxidant capacity of the compounds was examined, and molecular docking studies were performed to determine whether the sulfur, thymol or heterocyclic moieties interact with the Cu ions in tyrosinase, a type-3 copper enzyme. Using the CUPRAC assay, eight compounds (5–8, 10, 15–17) showed equal or better Cu (II) reducing capacity than trolox at neutral pH, with trolox equivalent antioxidant capacity (TEAC) coefficients ranging between 1.00 and 1.48. The compounds containing a thiadiazole moiety were most effective, with the methyl thiadiazole derivative (8) having the highest Cu(II) reducing capacity. Molecular docking studies of the sulfide derivatives with tyrosinase revealed that there were no direct interactions between the sulfur atom and the active site copper ions. However, the compounds displayed two different binding interactions with the histidine-Cu catalytic center. For compounds 4–13, the thymol portion was embedded in the active site cavity, while for compounds 14–17 the heterocyclic portion of the molecule approached the cavity.
Synthesis of thymol-based pyrazolines: An effort to perceive novel potent-antimalarials
Raghuvanshi, Dushyant Singh,Verma, Narsingh,Singh, Shiv Vardan,Khare, Sonam,Pal, Anirban,Negi, Arvind Singh
supporting information, (2019/05/01)
A series of thymol based substituted pyrazolines and chalcones was synthesized and evaluated for antimalarial activity, using in-vitro and in-vivo malaria models. All the target compounds (5a-k and 6a-j)were found to be active against human malaria parasite strain Plasmodium falciparum NF54. Among all, compounds 5e and 5f of chalcone series and 6c and 6f of pyrazoline series exhibited prominent antimalarial activity with IC50 less than 3 and 2 μM respectively, while other pyrazolines also significantly inhibited the P. falciparum with IC50 less than 10 μM. The designed pharmacophores were found to be effective against P. falciparum. Compound 6f was found to be able to retard malaria progression in mice. This was evident through decreased parasitemia, increased mean survival time and hemoglobin content in the treated animals. Moreover, 6f was observed as an inhibitor of heme polymerization pathway of the malaria parasite. It also inhibited free heme degradation, which could be possibly responsible for higher reactive oxygen species (ROS)in parasite, thus inhibiting the rapid proliferation of the parasite. In addition to this, compound 6f was found to be non-toxic with a good selectivity index. Based on these observations, the compound 6f could be taken up for further antimalarial lead optimization studies.
