Perspectives on medicinal properties of natural phenolic monoterpenoids and their hybrids.

Carvacrol, thymol and eugenol belong to a class of naturally presenting phenols with a ten-carbon unit, which are present in essential oils of many plants. These versatile molecules are incorporated as useful ingredients in many food products and find applications in agricultural, pharmaceutical, fragrance, cosmetic, flavor and other industries. They are wide ranging of biological and pharmaceutical activities: anti-inflammatory, antimicrobial, analgesic, anticancer and antioxidant. This review summarizes pharmacological and medicinal activities of these phytochemicals and their synthetic hybrids.

Hybrid molecules of carvacrol and benzoyl urea/thiourea with potential applications in agriculture and medicine.

Benzoyl phenyl urea, a class of insect growth regulator's acts by inhibiting chitin synthesis. Carvacrol, a naturally occurring monoterpenoid is an effective antifungal agent. We have structurally modified carvacrol (2-methyl-5-[1-methylethyl] phenol) by introducing benzoylphenyl urea linkage. Two series of benzoylcarvacryl thiourea (BCTU, 4a-f) and benzoylcarvacryl urea (BCU, 5a-f) derivatives were prepared and characterized by elemental analysis, IR, (1)H and (13)C NMR and Mass spectroscopy. Derivatives 4b, 4d, 4e, 4f and 5d, 5f showed comparable insecticidal activity with the standard BPU lufenuron against Dysdercus koenigii. BCTU derivatives 4c, 4e and BCU 5c showed good antifungal activity against phytopathogenic fungi viz. Magnaporthe grisae, Fusarium oxysporum, Dreschlera oryzae; food spoilage yeasts viz. Debaromyces hansenii, Pichia membranifaciens; and human pathogens viz. Candida albicans and Cryptococcus neoformans. Compounds 5d, 5e and 5f showed potent activity against human pathogens. Moderate and selective activity was observed for other compounds. All the synthesized compounds were non-haemolytic. These compounds have potential application in agriculture and medicine.

Design and development of novel insect growth regulators: synthesis, characterization and effect of benzoyl thymyl thioureas and ureas on total haemocyte count of Dysdercus koenigii.

Insect-growth regulators (IGRs) have been receiving foremost attention as potential means of selective insect control. Benzoyl phenyl urea (BPU) is a well-known IGR having chitin synthesis inhibitor activity. Mimics of BPU have been synthesized by suitable derivatization of a naturally occurring monoterpenoid, thymol (2-isopropyl-5-methyl phenol) to form a = series of substituted benzoyl thymyl thioureas (BTTUs) [IVa-f] and benzoyl thymyl ureas (BTUs) [Va-f]. The synthesized compounds have been characterized by (1)H and (13)C NMR, LC-MS and elemental analysis. These derivatives have been screened for their effect on total haemocyte count of Dysdercus koenigii. It has been observed that the introduction of substituted benzoyl thiourea and urea linkage into a thymol ring via an amino group results in higher activity than the parent compound thymol and a comparable pattern of results with the standard insect-growth regulators, Penfluron. Urea [Va-f] compounds exhibited greater effect on Total Haemocyte Count (THC) than thiourea [IVa-f]. Fluoro substitution enhanced the effect on THC more than chloro substituted compounds, while ortho-substitution resulted in a better effect than para-substitution. The results described in this paper are promising and provide new array of synthetic chemicals that may be utilized as insect growth regulators.

(Z)-2-(2-Isopropyl-5-methyl-phen-oxy)-N'-(2-oxoindolin-3-yl-idene)acetohydrazide.

In the title Mannich base, C(20)H(21)N(3)O(3), an isatin derivative of thymol, the O-CH(2)-C(=O)-N(H)-N fragment connect-ing the aromatic and fused-ring systems is approximately planar, with the N-N single bond in a Z configuration. The amino H atom of this N-N fragment is intra-molecularly hydrogen bonded to the carbonyl O atom of the indolinone fused ring as well as to the phen-oxy O atom of the aromatic ring. The amino H atom of the indoline fused ring forms a hydrogen bond with the double-bond O atom of an adjacent mol-ecule, this hydrogen bond giving rise to a linear chain motif.