Search

A series of new substituted 1,3-thiazole derivatives 10a-h were prepared via the reaction of monothiocarbohydrazones 8a-h with one equivalent of α-bromoketones in ethanol. Similarly, another series of new substituted 1,3,4-thiadiazines 11a-e were prepared from the reaction of monothiocarbohydrazones 8i,j with one equivalent of α-bromoketones in ethanol. The resulting products were obtained as colored crystals in moderate to good yields. All new compounds are fully characterized by 1H-, 13C-NMR, IR and elemental analysis. Pharmacophore modeling study of four of the synthesized compounds revealed that at least two of them have potential biological activities. Some of these activities will be investigated experimentally in the lab.

A series of 1,3 and 1,4-bis[5-(R-sulfanyl)-1,2,4-triazol-3-yl)benzene derivatives were synthesized by the reaction of isophthalic and terephthalic acid hydrazides with methyl and aryl isothiocyanates, followed by base-catalyzed cyclization and alkylation of the resulting bis-triazolethiols with alkyl bromides. The suggested obesity–colorectal cancer association initiated evaluation of the antiproliferative activity of the newly synthesized compounds against a panel of obesity-related colorectal cells and inhibition of pancreatic lipase (PL). In vitro enzymatic, colorimetric, and cell culture bioassays were carried out with respective reference agents. Among the tested compounds, 1,3-bis{5-[(4-bromobenzyl)sulfanyl]-4-methyl-4H-1,2,4-triazol-3-yl}benzene showed clearly promising, though unselective, cytotoxicity in HT29, HCT116, SW620, CACO2, and SW480 cancer cells with a PL-IC50 value of 9.57±1.21 μM (

Volatile oils from flowers and leaves of C. creticus L. and C. salviifolius L. were extracted by two extraction methods; namely, hydrodistillation and solid-phase micro-extraction (SPME). The chemical composition of essential oils was analyzed by GC and GC–MS. The volatile extracted from leaves and flowers of C. criticus using SPME was dominated by monoterpenes and sesquiterpenes hydrocarbon with α-pinene, camphene and α-cubebene as major components. In hydrodistillation, the oil extracted from leaves was dominated by oxygenated diterpenes and diterpenes hydrocarbon with manoyl oxide and sclarene as major components, whereas, the oil extracted from flowers was dominated by oxygenated diterpenes and diterpenes hydrocarbon with manoyl oxide and abietatriene as major components. The volatile from flowers and leaves of C. salviifolius obtained by SPME were dominated by monoterpenes and sesquiterpenes with δ-3-carene, α-pinene, β-pinene, and E-caryophyllene as major constituents. On the other hand, the oils from flowers and leaves of C. salviifolius obtained by hydrodistillation were dominated by oxygenated diterpenes, diterpenes hydrocarbon and esters with dehydro abietol, abietol, manoyl oxide and methyl octadecenoate as major components. In the leaves, the major components of the oil were manoyl oxide, E-ethyl cinnamate, and Z-ethyl cinnamate. These oils showed weak antioxidant activity when compared to the positive controls α-tocopherol, ascorbic acid, and EDTA, while the crude extracts aq. MeOH, butanol, and water showed good antioxidant activity. Discriminating between the studied plants based on the extraction method was also possible upon applying Principle component analysis (PCA) to the obtained GC–MS data.

Investigation of the chemical constituents of Salvia judaica growing wild in Jordan led to the isolation and identification of 15 known compounds. These included: luteolin-3'-methyl ether (1), indole-3-carboxyaldehyde (2), p-hydroxybenzaldehyde (3), tricin (4), apigenin (5), methyl isoferuloyl-7-(3,4-dihydroxyphenyl) lactate (6), methyl rosmarinate (7), rosmarinic acid (8), salvigenin (9), β-sitosterol (10), 3β, 28-dihydroxyurs-12-ene (11), cirsilineol (12), 2,3-dihydroxyurs-12-en-28-oic acid (13), β-sitosteryl glucoside (14), and tormentic acid (15). Compounds 6 and 7 exhibited strong radical scavenging and chelating activities as compared to α-tocopherol and ascorbic acid, compound 7 showed a 2-fold greater antioxidant activity as compared to compound 6. Furthermore, low doses of compounds 6 and 7 were able to inhibit the growth of leukemic (HL-60, Jurkat, K562 and CCRF-SB) and solid tumor cells (MCF-7, MDA-MB-231 and Caco-2). Compound 7 showed a ca. 3-4-fold stronger cytotoxicity against the tested cells as compared to compound 6.

A one-pot, three-component protocol for the synthesis of novel five-membered thiazole ring bonded to two hydrazone motifs is described. The acid-catalyzed reaction of one equivalent of thiocarbohydrazide, two equivalents of aromatic aldehydes, and one equivalent of phenacyl bromides afforded the five-membered thiazole ring. The reactions proceed with novel chemoselectivity. Similar reported protocols have always afforded 1,3,4-thiadiazines. The financial support of this work by the Deanship of Graduate Studies and Research at Yarmouk University is highly acknowledged (project no. 29/2014).

Triacylium salts 5 reacted with nine equivalents of dialkylcarbodiimide to give substituted tris(3,4,5,6-tetrahydro-1,3,5-triazinium) salts 6a-e. However, triacylium salts 5 reacted with six equivalents of N,N-dialkylcyanamide to give amino-substituted tris(1,3,5-oxadiazinium) salts 7a-e.

1,3,5-Tris(5-substituted-1,3,4-oxadiazol-2-yl)benzenes were prepared by the dehydration of the corresponding hydrazides. The structures of these compounds were elucidated by IR, 1H and 13C NMR spectroscopy. © 1997 John Wiley & Sons, Ltd.

Dehydration of N,N′-diacylalkanedioic acid dihydrazides with phosphoryl chloride gave 5,5′-disubstituted-2,2′-(1,n-alkanediyl)bis-1,3,4-oxadiazoles. The structures of these compounds were elucidated by 1H, 13C NMR, UV and IR spectroscopy.

N,N′-Diacyl acid dihydrazides were prepaed by the reaction of acid dihydazides with two equivalents of acyl chlorides. The structures of these compounds were elucidated by 1H and 13C NMR spectroscopy.

Substituted bis-1,3,4-oxadiazoles 3a-1 have been synthesized from the cyclization of N,N'-diaroyl or N,N'-dialkanoyl diacyl hydrazides, in presence of phosphorus oxychloride. A11 new compounds have been identified by 1H-NMR 13C-NMR and elemental analysis.

(1990). RECENT ADVANCES IN THE USE OF ACYLIUM SALTS IN ORGANIC SYNTHESIS. A BRIEF REVIEW. Organic Preparations and Procedures International: Vol. 22, No. 1, pp. 1-36.

Phenylmalonic acid dihydrazide reacted with 2,4-pentanedione to give, unexpectedly, 5,7-dimethyl-1,3-dioxo-2-phenyl-2,3-dihydro-1H-pyrazolo[1,2-a]pyrazole-4-ylium 5. The structure of the product is confirmed by X-ray crystallography.

(1990). RECENT ADVANCES IN THE USE OF ACYLIUM SALTS IN ORGANIC SYNTHESIS. A BRIEF REVIEW. Organic Preparations and Procedures International: Vol. 22, No. 1, pp. 1-36.

N-(Chlorosulfinyl)diarylketimines 1a–c readily react with alcohols, phenols and thiophenol to give good yields of dialkyl sulfites, diaryl sulfites and dithiosulfites, respectively, besides (diarylmethylene)ammonium chlorides 3a–c. The reactions of 1a with water and carboxylic acids have also been studied.

Dehydration of N,N′-diaroylbutanodihydrazides 3a–f with phosphoryl chloride gave, unexpectedly, 2,5-diaryl-1,3,4-oxadiazoles 4a–f. However, dehydration of N,N′-dialkanoylbutanodihydrazides 1a–c afforded 5,5′-dialkyl-2,2′-(1,2-ethandiyl)-bis(1,3,4-oxadiazoles) 2a–c.

N-(Chlorosulfinyl)diarylketimines 1a–c readily react with alcohols, phenols and thiophenol to give good yields of dialkyl sulfites, diaryl sulfites and dithiosulfites, respectively, besides (diarylmethylene)ammonium chlorides 3a–c. The reactions of 1a with water and carboxylic acids have also been studied.

Aliphatic and aromatic acid chlorides react with dialkylcyanamides in the presence of Lewis acid at low temperature. The reaction proceeds via a stepwise mechanism to afford 1,3,5-oxadiazinium salt in good yields.

Trimethyl phosphite selectively removes the N-1-oxygen in N-(3-methyl-2-quinoxaloyl) L-α-amino ester-1,4-dioxides, whereas it removes the N-4-oxygen in the corresponding series of dioxides lacking the C3-Me. This selectivity reversal reflects the relative strength of the intrahydrogen-bridging to the N-1-oxygen. The monoxides having the favourable N-oxygen are not reduced to the quinoxalines, implying that the reagent requires doubling of the N-oxide function for deoxygenation. However, alkaline sodium dithionite removes the N-1-oxygen in both series of the amino acid-dioxides, as well as in the parent quinoxaline-2-carboxylic acid-dioxides, a result that contradicts the report stating removal of the N-4-oxygen. The N-oxygenated quinoxalinium ion (me 145 or 159) prevails in the MS of the 4-oxides, but it is not observed (

N-Chlorosulfinyl diarylketimine reacts with Lewis acids to give an orange precipitate of l-oxa-2-thia-3-azabutatrienium salts. The latter compounds readily react with two equivalents of dialkylcarbodiimides to afford good yields of l-oxo-1,2,4,6-thiatriazinium salts, 3.

N-Chlorosulfinyl diarylketimine reacts with Lewis acids to give an orange precipitate of l-oxa-2-thia-3-azabutatrienium salts. The latter compounds readily react with two equivalents of dialkylcarbodiimides to afford good yields of l-oxo-1,2,4,6-thiatriazinium salts, 3.

Diacyl chlorides react with dialkylcyanamide in the presence of a Lewis acid to give amino-substituted bis-1,3,5-oxadiazinium salts in excellent yields. A mechanism leads to the formation of the product has been postulated. All new compounds have been characterized by 1H-nmr, 13C-nmr, ir-spectroscopy and elemental analysis.