- An efficient one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazoles from aldehydes and hydrazides using Lawesson’s reagent
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Five-membered heterocyclic-ring systems, such as thiadiazoles, remain an important and prevalent scaffold in the development of novel leads in medicinal chemistry for a variety of therapeutic targets. A two-step, one-pot synthesis of 2,5-disubstituted-1,3,4-thiadiazole derivatives from aryl hydrazides and aryl aldehydes using Lawesson’s reagent is described, yielding 2,5-disubstituted-1,3,4-thiadiazoles in moderate-to-high yields. Based on preliminary biological experiments, some of the newly synthesized thiadiazoles show antioxidant activity.
- Ko, Inseok,Park, Soojin,Lee, Goeun,Kim, Hakwon
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- Transition-metal-free oxidative iodination of 1,3,4-oxadiazoles
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Transition-metal-free oxidative iodination of 2-substituted 1,3,4-oxadiazoles was achieved by using sodium iodide as the halide source and Selectfluor as the oxidant. Variously substituted products were obtained in moderate to good yields under operationa
- Dannenberg, Carl Albrecht,Bizet, Vincent,Zou, Liang-Hua,Bolm, Carsten
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supporting information
p. 77 - 80
(2015/02/02)
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- Synthesis and biological evaluation of 5′-phenyl-3′H-spiro- [indoline-3,2′-[1,3,4]oxadiazol]-2-one analogs
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A series of 5′-phenyl-3′H-spiro[indoline-3,2′-[1,3,4] thiadiazol]-2-one analogs were synthesized and their Bcl-2 protein inhibitory activities were studied. The lead compound was originally identified using a fluorescence polarization-based competitive binding assay. Among the 10 compounds investigated, 1k showed good binding affinities to Bcl-xL and Mcl-1, with inhibition constants of 8.9 μmol/L and 3.4 μmol/L, respectively. While compound 1c achieved tight binding affinities to Bcl-xL (Ki = 0.16 μmol/L), has the potential to be a new lead compound.
- Liu, Hua-Quan,Wang, De-Cai,Wu, Fei,Tang, Wei,Ouyang, Ping-Kai
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p. 929 - 933
(2013/09/24)
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- Syntheses and antitumor activities of N′1, N′3-dialkyl-N′1,N′3-di- (alkylcarbonothioyl) malonohydrazide: The discovery of elesclomol
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A series of N′1,N′3-dialkyl- N′1,N′3-di(alkylcarbonothioyl) malonohydrazides have been designed and synthesized as anticancer agents by targeting oxidative stress and Hsp70 induction. Structure-activity relationship (SAR) studies lead to the discovery of STA-4783 (elesclomol), a novel small molecule that has been evaluated in a number of clinical trials as an anticancer agent in combination with Taxol.
- Chen, Shoujun,Sun, Lijun,Koya, Keizo,Tatsuta, Noriaki,Xia, Zhiqiang,Korbut, Timothy,Du, Zhenjian,Wu, Jim,Liang, Guiqing,Jiang, Jun,Ono, Mitsunori,Zhou, Dan,Sonderfan, Andrew
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p. 5070 - 5076
(2013/09/12)
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- THERAPEUTIC COMPOUNDS AND METHODS
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The invention provides compounds of formula I: and salts thereof. The invention also provides pharmaceutical compositions comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I and therapeutic methods for treating cancer using compounds of formula I.
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- Cobalt(III) complexes of some aromatic thiohydrazides - Synthesis, characterization and structure
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[Co(NH3)5Cl]Cl2 forms neutral 1:3 complex by reaction with aromatic thiohydrazides, i.e. thiobenzhydrazide, o-hydroxythiobenzhydrazide, thiophen-2-thiohydrazide and furan-2-thiohydrazide. All these complexes are diamagneti
- Basak, Prodyut,Gangopadhyay, Snigdha,De, Sudipta,Drew,Gangopadhyay, Pijush Kanti
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experimental part
p. 1495 - 1499
(2010/07/05)
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- Design, synthesis, and characterization of new iron chelators with anti-proliferative activity: Structure-activity relationships of novel thiohydrazone analogues
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Di-2-pyridylketone isonicotinoyl hydrazone Fe chelators utilize the N,N,O-donor set and have moderate anti-proliferative effects. Their closely related N,N,S-thiosemicarbazone analogues, namely, the di-2-pyridylketone thiosemicarbazones, exhibit markedly
- Kalinowski, Danuta S.,Sharpe, Philip C.,Bernhardt, Paul V.,Richardson, Des R.
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p. 6212 - 6225
(2008/04/05)
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- 5′-Phenyl-3′H-spiro[indoline-3,2′-[1,3,4]thiadiazol]-2-one inhibitors of ADAMTS-5 (Aggrecanase-2)
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5′-Phenyl-3′H-spiro[indoline-3,2′-[1,3,4]thiadiazol]-2-one inhibitors of ADAMTS-5 (Aggrecanase-2) have been prepared via commercially available starting materials. Selected compounds 23, 33-35 show sub-micromolar ADAMTS-5 potency and strong SAR trends with selectivity over the related metalloproteases ADAMTS-4 (Aggrecanase-1), MMP12, and MMP13. This series of compounds represents progress toward a selective ADAMTS-5 inhibitor as a disease modifying osteoarthritis drug.
- Bursavich, Matthew G.,Gilbert, Adam M.,Lombardi, Sabrina,Georgiadis, Katy E.,Reifenberg, Erica,Flannery, Carl R.,Morris, Elisabeth A.
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p. 5630 - 5633
(2008/03/14)
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- THIADIAZOLINE DERIVATIVES
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An antitumor agent comprising a thiadiazoline derivative represented by the general formula (I), or a pharmacologically acceptable salt thereof as an active ingredient: (wherein Z represents a sulfur atom and the like, R1 represents substituted or unsubstituted lower alkynyl and the like, R2 represents a hydrogen atom and the like, R3 represents substituted or unsubstituted lower alkyl and the like, and R4 represents substituted or unsubstituted aryl and the like), and the like are provided.
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Page/Page column 32-33
(2010/11/08)
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- COMPOUNDS, METHODS AND FORMULATIONS FOR THE ORAL DELIVERY OF A GLUCAGON LIKE PEPTIDE (GLP)-1 COMPOUND OR AN MELANOCORTIN 4 RECEPTOR (MC4) AGONIST PEPTIDE
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The present invention relates to novel compounds, methods, and formulations useful for the oral delivery of a GLP-1 compound or an MC4 agonist peptide.
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Page/Page column 24
(2008/06/13)
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- Reactions of trichloromethylarenes with hydrazine derivatives. Synthesis of 2,5-disubstituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles
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The effect of the solvent on the course of the reaction between trichloromethylarenes and thioacylhydrazines or acylhydrazines has been considered. In alcohols as solvents, alkyl arenecarboxylates form as a result of alcoholysis, while 2,5-disubstituted 1,3,4-thiadiazoles (1,3,4-oxadiazoles) form as minor products. In pyridine solutions, the major or sole products are those of reductive condensation, i.e., the corresponding N-substituted hydrazones of arenecarbaldehydes. 1,3,4-Thiadiazole or 1,3,4-oxadiazole derivatives are obtained in good yield when the reaction is carried out in a pyridine - alkanol mixture.
- Poddubnyi,Belen'kii,Krayushkin
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p. 1185 - 1188
(2007/10/03)
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- Halopropargyl compounds, compositions, uses and processes of preparation
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Compounds of the formula STR1 wherein A is selected from the group consisting of hydrogen, alkyl, aryl, and heterocyclic; Y and Z are independently selected from the group consisting of O, S, and N--R; R is selected from the group consisting of hydrogen,
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- HETEROCYCLIZATION OF DERIVATIVES OF THIONCARBOXYLIC ACIDS TO 1,3,4-THIADIAZOLES UNDER THE ACTION OF TERT-BUTYL HYPOCHLORITE
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A method for synthesis of 2-alkyl-5-aryl- and 2,5-diaryl-1,3,4-thiadiazoles by successive reaction of thioamides with tert-butyl hypochlorite and benzothiohydrazides was developed.The first step in the formation of 1,3,4-thiadiazoles consists of oxidation
- Demchuk, D. V.,Lutsenko, A. I.,Troyanskii, E. I.,Nikishin, G. I.
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p. 1690 - 1695
(2007/10/02)
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- Substituted 1,3,4-Thiadiazoles with Anticonvulsant Activity. 2. Aminoalkyl Derivatives
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This paper describes the synthesis and pharmacological evaluation of a number of substituted 1,3,4-thiadiazoles.The first member of the series, 2-(aminomethyl)-5-(2-biphenylyl)-1,3,4-thiadiazole (7) was found to possess potent anticonvulsant properties in rats and mice and compared favorably with the standard anticonvulsant drugs phenytoin, phenobarbital, and carbamazepine in a number of test situations.The potency of compound 7 was maintained on alkylation of the side-chain nitrogen atom; however, aryl substitution or chain lengthening caused a drop in potency.Replacement of the 2-biphenylyl group by phenyl or benzyl also lead to inactive compounds.
- Stillings, Michael R.,Welbourn, Anthony P.,Walter, Donald S.
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p. 2280 - 2284
(2007/10/02)
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- SEMICARBAZONES AND THIOSEMICARBAZONES OF THE HETEROCYCLIC SERIES. XLIV. CYCLIZATION OF ISATIN AND 1-ACETYLISATIN 3-THIOBENZOYLHYDRAZONES
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Isatin 3-thiobenzoylhydrazone undergoes cyclization with the addition of the sulfur atom to the C3 atom and closure of the thiadiazole ring.In contrast, 3-thioaroylhydrazones of 1-acetylisatin undergo cyclization with participation of C2 and close the thiadiazine ring with the formation of derivatives of the new heterocyclic system thiadiazinoindole.
- Tomchin, A.B.
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p. 504 - 510
(2007/10/02)
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- Studies on Organophosphorus Compounds. XXXIV. Syntheses of 2,3-Dihydro-1,3,4,2-Thiadiazaphospholes and Thiohydrazides
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N'-Substituted hydrazides, 2, react with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide, 1, in refluxing benzene to give 2,3-dihydro-1,3,4,2-thiadizaphospholes, 3; in one case also the thiohydrazide, 4e, was isolated.Benzohydrazide, 10
- El-Barbary, A. A.,Scheibye, S.,Lawesson, S.-O.,Fritz, H.
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p. 597 - 602
(2007/10/02)
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