81188-34-3

Upstream product

• 19430-32-1 2-Chloro-5-(4-nitrophenyl)-1,3,4-thiadiazole 
• 84459-83-6 potassium 2-(4-nitrobenzoyl)hydrazinecarbodithioate 
• 636-97-5 N-amino-(4-nitrophenyl)carboxamide 
• 75-15-0 carbon disulfide 
• 62-23-7 4-nitro-benzoic acid 
• 99-77-4 ethyl 4-nitrobenzoate 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 833-63-6 5-(4-nitrophenyl)-1,3,4-thiadiazol-2-amine 

Downstream Products

• 207236-15-5 2-ethylsulfanyl-5-(4-nitro-phenyl)-[1,3,4]thiadiazole 
• 97051-25-7 2-Ethanesulfonyl-5-(4-nitro-phenyl)-[1,3,4]thiadiazole 
• 1041361-50-5 C₁₂H₁₃N₃O₄S₃ 
• 1041361-32-3 C₁₂H₁₃N₃O₂S₃ 
• 1172580-93-6 C₂₂H₂₄BrN₃O₅S₂ 
• 1374831-12-5 C₁₅H₆F₃N₅O₂S₃ 
• 91096-52-5 [5-(4-Nitro-phenyl)-[1,3,4]thiadiazol-2-yl]-hydrazine 
• 1447767-46-5 C₁₅H₁₁N₅O₂S 
• 1186014-30-1 C₁₆H₁₃N₅O₃S 
• 1186014-29-8 C₁₅H₁₁N₅O₃S 
• 136071-32-4 Zn((C₆H₄NO₂)(CS)2N₂)2 

Relevant academic research and scientific papers

Development of Novel (+)-Nootkatone Thioethers Containing 1,3,4-Oxadiazole/Thiadiazole Moieties as Insecticide Candidates against Three Species of Insect Pests

To improve the insecticidal activity of (+)-nootkatone, a series of 42 (+)-nootkatone thioethers containing 1,3,4-oxadiazole/thiadiazole moieties were prepared to evaluate their insecticidal activities against Mythimna separata Walker, Myzus persicae Sulzer, and Plutella xylostella Linnaeus. Insecticidal evaluation revealed that most of the title derivatives exhibited more potent insecticidal activities than the precursor (+)-nootkatone after the introduction of 1,3,4-oxadiazole/thiadiazole on (+)-nootkatone. Among all of the (+)-nootkatone derivatives, compound 8c (1 mg/mL) exhibited the best growth inhibitory (GI) activity against M. separata with a final corrected mortality rate (CMR) of 71.4%, which was 1.54- and 1.43-fold that of (+)-nootkatone and toosendanin, respectively; 8c also displayed the most potent aphicidal activity against M. persicae with an LD50 value of 0.030 μg/larvae, which was closer to that of the commercial insecticidal etoxazole (0.026 μg/larvae); and 8s showed the best larvicidal activity against P. xylostella with an LC50 value of 0.27 mg/mL, which was 3.37-fold that of toosendanin and slightly higher than that of etoxazole (0.28 mg/mL). Furthermore, the control efficacy of 8s against P. xylostella in the pot experiments under greenhouse conditions was better than that of etoxazole. Structure-activity relationships (SARs) revealed that in most cases, the introduction of 1,3,4-oxadiazole/thiadiazole containing halophenyl groups at the C-13 position of (+)-nootkatone could obtain more active derivatives against M. separata, M. persicae, and P. xylostella than those containing other groups. In addition, toxicity assays indicated that these (+)-nootkatone derivatives had good selectivity to insects over nontarget organisms (normal mammalian NRK-52E cells and C. idella and N. denticulata fries) with relatively low toxicity. Therefore, the above results indicate that these (+)-nootkatone derivatives could be further explored as new lead compounds for the development of potential eco-friendly pesticides.

Efficient formation of C–S bond using heterocyclic thiones and arynes

Phenylthio heterocyclic compounds are widely used because of their diverse biological activities and medicinal prospects. Here, a facile method was reported. An arylation of 1,3,4-oxa(thia)diazol-2-thiones reacting with arynes to build C(aryl)-S bonds in the presence of CsF had good yields and excellent selectivity. The reaction was completed in short time without using expensive reagents and catalysts. Present reaction system is an efficient procedure to process phenylthio heterocyclic compounds and reveals a sustainable method and better application prospects in future organic synthesis.

Synthesis and biological evaluation of novel disulfides incorporating 1,3,4-thiadiazole scaffold as promising antitumor agents

In the present study, fourteen 2,5-disubstituted 1,3,4-thiadiazole derivatives containing disulfide group were prepared. The resulting compounds 7a–7n were identified by IR, NMR, MS, and elemental analysis. Their antiproliferative properties in vitro were studied employing standard CCK-8 assay against SMMC-7721, MCF-7, and A549 lines. Bioassay indicated that some compounds showed stronger antitumor effects than reference drugs PX-12 and 5-fluorouracil. Among these screened compounds, compound 7h showed excellent biological activities in inhibiting SMMC-7721 cell proliferation with IC50 at 1.93 ± 0.08 μM. Compounds 7k and 7i manifested highly effective growth inhibitory activity versus MCF-7 cells, with IC50 at 3.04 ± 0.09 and 3.54 ± 0.17 μM, respectively. For A549 cells, compound 7m was found to have the highest antitumor potency with IC50 at 3.67 ± 0.13 μM.

Synthesis and biological activities of benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety

A series of benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety were designed, synthesized and evaluated for their antibacterial, antifungal and antiviral activities. The bioassay results indicated that most of target compounds showed good antiviral activities against tobacco mosaic virus (TMV) and antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (Rs). Especially, the anti-Xoo effect of title compounds 5k (N-(5-methoxybenzo[d]thiazol-2-yl)-2-((5-(2-tolyl)-1,3,4-thiadiazol-2-yl)thio)acetamide) and the anti-Rs effect of title compounds 5a (N-(5-nitrobenzo[d]thiazol-2-yl)-2-((5-(4-(trifluorom ethyl)phenyl)-1,3,4-thiadiazol-2-yl)thio)acetmide) respectively reached 52.4% and 71.6% at 100 μg/mL, which are superior to that of bismerthiazol (32.0% and 52.3%). In addition, the protective and inactivation activities of title compound 5i (N-(5-methoxybenzo [d]thiazol-2-yl)-2-((5-(4-nitrophenyl)-1,3,4-thiadiazol-2-yl)thio)acetamide) against TMV were 79.5% and 88.3%, respectively, which are better than that of ningnanmycin (76.4% and 86.8%). The above research showed that benzothiazole derivatives bearing a 1,3,4-thiadiazole moiety may be used as potential molecular templates in searching for highly-efficient antiviral and antibacterial agents.

Development of 3,5-Dinitrobenzylsulfanyl-1,3,4-oxadiazoles and Thiadiazoles as Selective Antitubercular Agents Active Against Replicating and Nonreplicating Mycobacterium tuberculosis

Herein, we report the discovery and structure-activity relationships of 5-substituted-2-[(3,5-dinitrobenzyl)sulfanyl]-1,3,4-oxadiazoles and 1,3,4-thiadiazoles as a new class of antituberculosis agents. The majority of these compounds exhibited outstanding in vitro activity against Mycobacterium tuberculosis CNCTC My 331/88 and six multidrug-resistant clinically isolated strains of M. tuberculosis, with minimum inhibitory concentration values as low as 0.03 μM (0.011-0.026 μg/mL). The investigated compounds had a highly selective antimycobacterial effect because they showed no activity against the other bacteria or fungi tested in this study. Furthermore, the investigated compounds exhibited low in vitro toxicities in four proliferating mammalian cell lines and in isolated primary human hepatocytes. Several in vitro genotoxicity assays indicated that the selected compounds have no mutagenic activity. The oxadiazole and thiadiazole derivatives with the most favorable activity/toxicity profiles also showed potency comparable to that of rifampicin against the nonreplicating streptomycin-starved M. tuberculosis 18b-Lux strain, and therefore, these derivatives, are of particular interest.

1,2,4-TRIAZOLE, 1,3,4-OXADIAZOLE, AND 1,3,4-THIADIAZOLE DERIVATIVES AND THEIR ANTIMYCOBACTERIAL ACTIVITY

Disclosed herein are novel five membered heterocyclic compounds of Formula (I) wherein, X is S or SO2; n is 0, 1; m is1 or 2; Y is N, O or S; R2 independently represents H or alkyl or halo selected from -CI, -F; or -CF3, or -OH or-NH2 or - NO2; and R1 independently represents H or C1 to C5 straight or branched chain alkyl, alkenyl, alkynyl or a group -(CH2)5Br or pyrrolidine or - NHR' wherein R' is H or isopropyl or (II) or (III) which selectively act against dormant pathogenic tuberculi bacilli and exhibit antiproliferative activities and for treatment of a disease or disorder associated with GroEL1/GroEL2 activity. The invention relates to a process for preparation of novel five membered heterocyclic compounds of Formula I and to pharmaceutical compositions thereof.

Synthesis and spectral characterization of Zn(II) microsphere series for antimicrobial application

Microsphere series have been synthesized by reacting zinc(II) acetate dihydrate with Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole/oxadiazole/triazole with salicylaldehyde. Elemental analysis suggests that the complexes have 1:2 and 1:1 stoichiometry of the type [Zn(L)2(H2O)2] and [Zn(L′)(H 2O)2]; LH = Schiff bases derived from 2-hydrazino-5- [substituted phenyl]-1,3,4-thia/oxadiazole with salicylaldehyde; L′H 2 = Schiff bases derived from 3-(substituted phenyl)-4-amino-5- hydrazino-1,2,4-triazole and salicylaldehyde and were characterized by elemental analyses, IR, 1H NMR and 13C NMR spectral data. Scanning electron microscopy (SEM) showed that synthesized materials have microsphere like structure and there EDX analysis comparably matches with elemental analysis. For the antimicrobial application Schiff bases and their zinc(II) complexes were screened for four bacteria e.g. Bacillus subtilis, Pseudomonas aeruginosa, Salmonella typhi, Streptococcus pyogenes and four fungi e.g. Cyrtomium falcatum, Aspergillus niger, Fusarium oxysporium and Curvularia pallescence by the reported method. Schiff base and Zn(II) compounds showed significant antimicrobial activities. However, activities increase upon chelation. Thermal analysis (TGA) data of compound (10) showed its stability up to 300 °C.

Synthesis of new chiral 2,5-disubstituted 1,3,4-thiadiazoles possessing γ-butenolide moiety and preliminary evaluation of in vitro anticancer activity

A new series of chiral 1,3,4-thiadiazoles derivatives possessing γ-substituted butenolide moiety were synthesized and evaluated for in vitro anticancer properties. All the compounds showed good anticancer activities against Hela cell lines. Of all the studied compounds, compound 9e exhibited the best inhibitory activity with an IC50 of 0.9 μM. After being treated with 0.1 μg/mL compound 9e for 24 h, the growth inhibition rate of Hela cell lines was 59.2%.

Synthesis and anti-Helicobacter pylori activity of 5-(nitroaryl)-1,3,4-thiadiazoles with certain sulfur containing alkyl side chain

A series of 5-(nitroaryl)-1,3,4-thiadiazoles bearing certain sulfur containing alkyl side chain similar to pendent residue in tinidazole molecule were synthesized and evaluated against Helicobacter pylori using disk diffusion method. The synthesized compounds were also evaluated for their antibacterial, antifungal and cytotoxic effects. Study of the structure-activity relationships of this series of compounds indicated that both the structure of the nitroaryl unit and the pendent group on 2-position of 1,3,4-thiadiazole ring dramatically impact the anti-H. pylori activity. While compound 7a containing 2-[2-(ethylsulfonyl)ethylthio]-side chain from nitrothiophene series was the most potent compound tested against clinical isolates of H. pylori, however, nitroimidazoles 6c and 7c were found to be more promising compounds because of their respectable anti-H. pylori activity besides less cytotoxic effects.

Synthesis and antifungal activity of 2-aryl-1,3,4-thiadiazole-5-sulphides, sulphoxides and sulphones

2-Aryl-1,3,4-thiadiazole-5-sulphides, sulphoxides and sulphones were synthesized and tested against a variety of fungal strains, Miconazole and fluconazole were used as reference drugs. The most active compounds against Candida albicans, Candida spp., Cryptococcus neoformans and Aspergillus niger were 2-(1-methyl-5-nitro-2-imidazolyl)-5-methylsulphonyl-1 ,3,4-thiadiazole (8h) and 2-(5-nitro-2-furyl)-5-methylsulphonyl-1,3,4-thiadiazole (8f). Our results showed that compounds 8h and 8f were several times more active than fluconazole in most fungal strains.