72836-11-4

Usage

InChI:InChI=1/C9H8N4O2S2/c10-8-11-12-9(17-8)16-5-6-1-3-7(4-2-6)13(14)15/h1-4H,5H2,(H2,10,11)

Upstream product

• 100-14-1 4-nitrobenzyl chloride 
• 2349-67-9 2-Amino-5-mercapto-1,3,4-thiadiazole 
• 100-11-8 1-bromomethyl-4-nitro-benzene 

Downstream Products

• 868739-31-5 2-chloro-5-(4-nitro-benzylsulfanyl)-[1,3,4]thiadiazole 
• 1018970-34-7 C₁₆H₁₁FN₄O₃S₂ 
• 535964-66-0 C₁₆H₁₁ClN₄O₃S₂ 
• 530126-52-4 C₁₆H₁₁ClN₄O₃S₂ 
• 1220687-94-4 7-hydroxy-2-(p-nitrobenzylsulfanyl)-6-undecyl[1,3,4]thiadiazolo[3,2-a]benzimidazole-5,8-dione 
• 1222558-04-4 2-(p-nitrobenzylsulfanyl)-1-thia-3,3a,10-triazapentaleno[1,2-b]naphthalene-4,9-dione 
• 1242283-93-7 N-(5-((4-nitrobenzyl)thio)-1,3,4-thiadiazol-2-yl)nicotinamide 
• 1408325-25-6 C₃₁H₃₆N₄O₃S₃ 
• 1431555-12-2 N-deacetyl-N-({5-[(4-nitrobenzyl)sulfanyl]-1,3,4-thiadiazol-2-yl}carbamoyl propionyl) N-methyl colchiceinamide 
• 1384978-63-5 C₁₆H₁₀N₄O₃S₂Se 
• 868739-34-8 2-chloro-5-(4-nitro-phenylmethanesulfonyl)-[1,3,4]thiadiazole 

Relevant academic research and scientific papers

Synthesis and biological assessment of ciprofloxacin-derived 1,3,4-thiadiazoles as anticancer agents

The quinolone-3-carboxylic acid scaffold is essential structure for antibacterial activity of fluoroquinolones such as ciprofloxacin. Modification of 3-carboxylic functionality in this structure can be used for switching its activity from antibacterial to anticancer. Accordingly, a series of C-3 modified ciprofloxacin derivatives containing N-(5-(benzylthio)-1,3,4-thiadiazol-2-yl)-carboxamide moiety was synthesized as novel anticancer agents. Most of compounds showed significant activity against MCF-7, A549 and SKOV-3 cancer cells in the MTT assay. In particular, compounds 13a-e and 13g were found to be as potent as standard drug doxorubicin against MCF-7 cell line (IC50s = 3.26–3.90 μM). Furthermore, the 4-fluorobenzyl derivatives 13h and 14b with IC50 values of 3.58 and 2.79 μM exhibited the highest activity against SKOV-3 and A549 cells, being as potent as doxorubicin. Two promising compounds 13e and 13g were further tested for their apoptosis inducing activity and cell cycle arrest. Both compounds could significantly induce apoptosis in MCF-7 cells, while compound 13e was more potent apoptosis inducer resulting in an 18-fold increase in the proportion of apoptotic cells at the IC50 concentration in MCF-7 cells. The cell cycle analysis revealed that compounds 13e and 13g could increase cell portions in the sub-G1 phase, inducing oligonucleosomal DNA fragmentation and apoptosis confirmed by comet assay.

Discovery and development of substituted thiadiazoles as inhibitors of Staphylococcus aureus Sortase A

High-throughput screening of small-molecule libraries has led to the identification of thiadiazoles as a new class of inhibitors against Staphylococcus aureus sortase A (SrtA). N-(5-((4-nitrobenzyl)thio)-1,3,4-thiadiazol-2-yl)nicotinamide (IC50

Design, synthesis, and biological activity of novel myricetin derivatives containing amide, thioether, and 1,3,4-thiadiazole moieties

A series of myricetin derivatives containing amide, thioether, and 1,3,4-thiadiazole moieties were designed and synthesized, and their antiviral and antibacterial activities were assessed. The bioassays showed that all the title compounds exhibited potent in vitro antibacterial activities against Xanthomonas citri (Xac), Ralstonia solanacearum (Rs), and Xanthomonas oryzae pv. Oryzae (Xoo). In particular, the compounds 5a, 5f, 5g, 5h, 5i, and 5l, with EC50 values of 11.5–27.3 μg/mL, showed potent antibacterial activity against Xac that was better than the commercial bactericides Bismerthiazol (34.7 μg/mL) and Thiodiazole copper (41.1% μg/mL). Moreover, the in vivo antiviral activities against tobacco mosaic virus (TMV) of the target compounds were also tested. Among these compounds, the curative, protection, and inactivation activities of 5g were 49.9, 52.9, and 73.3%, respectively, which were better than that of the commercial antiviral Ribavirin (40.6, 51.1, and 71.1%, respectively). This study demonstrates that myricetin derivatives bearing amide, thioether, and 1,3,4-thiadiazole moieties can serve as potential alternative templates for the development of novel, highly efficient inhibitors against plant pathogenic bacteria and viruses.

Containing substituted 1, 3, 4-thiadiazole sulfide pyrazole amide and pyrazole imine derivatives and preparation method and application

The invention discloses pyrazole amide and pyrazole imine derivatives containing substituted 1, 3, 4-thiadiazole thioether as well as a preparation method and an application of the derivatives. The compounds have the structures as shown in formulae (I) and (II). The preparation method comprises the following steps: by taking substituted hydrazine as an initial raw material, carrying out closed loop, chlorine formylation, oxidation and chloro reaction to obtain pyrazole acyl chloride; carrying out a reaction on 2-amino-5-mercapto-1, 3, 4-thiadiazole and substituted benzyl chloride to obtain 2-amino-5-substituted 1, 3, 4-thiadiazole thioether; and then, carrying out a substitution reaction on 2-amino-5-substituted 1, 3, 4-thiadiazole thioether and substituted pyrazole acyl chloride to obtain the pyrazole amide compound (I) containing substituted 1, 3, 4-thiadiazole thioether; by taking substituted hydrazine as an initial raw material, carrying out closed loop and chlorine formylation to obtain pyrazole aldehyde; carrying out an additive elimination reaction on pyrazole aldehyde and 2-amino-5-mercapto-1, 3, 4-thiadiazole under a backflow condition of anhydrous ethanol to obtain 2-substituted pyrazole imidogen-5-mercapto-1, 3, 4-thiadiazole; and then carrying out a reaction on 2-substituted pyrazole imidogen-5-mercapto-1, 3, 4-thiadiazole and substituted benzyl chloride to generate the pyrazole imine compound (II) containing substituted 1, 3, 4-thiadiazole thioether. The compounds disclosed by the invention have a good inhibiting effect on tobacco mosaic virus and can be used for preparing anti-plant virus drugs.

Synthesis and cytotoxic evaluation of new colchicine derivatives bearing 1,3,4-thiadiazole moieties

In search of novel anticancer agents, a series of N-methyl colchiceinamide derivatives (7a-7i) containing 1,3,4-thiadiazole moieties were synthesized, and their structures were confirmed by spectral analysis. Cytotoxicity of these compounds was evaluated by MTT assay in vitro against four human tumor cell lines, i.e. A2780, A549, BEL7402, and MCF-7. The results indicated that most of the derivatives showed significant anticancer activities, particularly, compounds 7h and 7i showed more potent cytotoxic activities of all screened cancer cells than colchicine.

Synthesis and in vitro biological evaluation of farnesylthiosalicylic acid derivatives as anti-tumor carcinoma agents

Novel farnesylthiosalicylic acid (FTA) derivatives 5a-m with different substituted 1,3,4-thiadiazoles were synthesized. Compounds 5b, 5c, 5e and 5f displayed anti-tumor activities superior to FTA in most cancer cells tested. Furthermore, 5e induced tumor cell apoptosis, which was accompanied by lower Bcl-2 expression, but with higher Bax and caspase 3 expression activities in cancer cells.

Synthesis and in vitro antitumor activity of 1,3,4-thiadiazole derivatives based on benzisoselenazolone

A series of novel 1,3,4-thiadiazole derivatives based on benzisoselenazolone were synthesized and evaluated for their cytotoxicity in vitro against human liver cancer cell SSMC-7721, human breast cancer cell MCF-7 and human lung cancer cell A549 by CCK-8 assay. The results showed that compounds 7e, 7f, 7h, 7k, 7l and 7m displayed good cytotoxicity against MCF-7 cell lines. Compound 7l exhibited the most potent antitumor activities among the tested compounds.

Synthesis of 2-alkyl/arylalkyl/phenacylsul-fanyl-1 -thia-3,3, 10-triaza-pentaleno[ 1,2-b]naphthalene-4,9-dione

2,3-Dichloronaphthoquinone is condensed with 5-(alkyl/arylalkyl/ phenacylthio)-1,3,4-thiadiazol-2-amine in acetic acid to furnish a novel and hitherto unknown 2-alkyl/aralkyl/phenacylsulfanyl-1-thia-3,3a,10-triaza- pentaleno[1,2-b]naphthalene-4,9-dione. The structure of the synthesized compound has been confirmed by converting it into the corresponding reductive acetate. The structures of newly prepared compounds have been confirmed by analytical and spectral data.

Design and synthesis of thiadiazoles and thiazoles targeting the Bcr-Abl T315I mutant: From docking false positives to ATP-noncompetitive inhibitors

(Figure Presented) Overcoming resistance: In an effort to optimize our previously identified dual Src/Abl hits, a new series of 1,3,4-thiadiazoles and 1,3-thiazoles were designed and synthesized, paying particular attention to the reduction of their lipophilicity and to the improvement of the affinity towards the drug-resistant T315I mutant. Compound 5 was identified as a promising allosteric inhibitor of the T315I mutant.

Discovery and SAR of 1,3,4-thiadiazole derivatives as potent Abl tyrosine kinase inhibitors and cytodifferentiating agents

A series of substituted benzoylamino-2-[(4-benzyl)thio]-1,3,4-thiadiazoles has been discovered as potent Abl tyrosine kinase inhibitors. Molecular docking simulations on the Abl tyrosine kinase were conducted in order to rationalize the SAR of the synthesized inhibitors. The most active compound identified from the enzymatic screening (6a) showed interesting inhibitory activity on Imatinib-sensitive murine myeloid 3B clone and Bcr-Abl-independent Imatinib-resistant leukemia cells. Surprisingly, 6a was also proved to act as differentiating inducers in human promyelocytic leukemia cells (HL-60).