13581-25-4

Usage

Uses

Used in Medicinal Chemistry:
5-(4-pyridyl)-3H-1,3,4-thiadiazole-2-thione is used as a pharmacological agent for its antifungal and antibacterial activities, making it a valuable component in the development of new drugs to combat infections.
Used in Synthesis of Biologically Active Compounds:
As a building block, 5-(4-pyridyl)-3H-1,3,4-thiadiazole-2-thione is used in the synthesis of other compounds with potential biological activities, contributing to the discovery of novel therapeutic agents.
Used in Agricultural Pesticides:
5-(4-pyridyl)-3H-1,3,4-thiadiazole-2-thione is studied for its potential use in the development of agricultural pesticides, indicating its possible role in creating more effective and targeted pest control solutions.
Used in Research and Development:
5-(4-pyridyl)-3H-1,3,4-thiadiazole-2-thione is of interest to researchers and chemists for its diverse range of potential applications and biological activities, driving further exploration and innovation in various scientific fields.

Upstream product

• 62295-00-5 thioisonicotinic acid hydrazide 
• 54-85-3 isoniazid 
• 75-15-0 carbon disulfide 
• 2196-13-6 pyridine-4-carbothioamide 
• 1570-45-2 isonicotinic acid ethylester 
• 2459-09-8 4-pyridinecarboxylic acid, methyl ester 
• 55-22-1 pyridine-4-carboxylic acid 
• 61019-32-7 potassium 4-pyridinyldithiocarbazate 
• 108103-05-5 dithioisonicotinic acid ; potassium-salt 

Downstream Products

• 134129-56-9 2-Pyridin-4-yl-6-(triphenyl-λ⁵-phosphanylidene)-4H-[1,3,4]thiadiazine-5-thione 
• 1172580-96-9 C₂₁H₂₄BrN₃O₃S₂ 

Relevant academic research and scientific papers

Linked pyridinyl-thiadiazoles: Design and synthesis as potential candidate for treatment of XDR and MDR tuberculosis

Abstract Multi-drug resistant (MDR) and extremely drug resistant (XDR) Mycobacterium tuberculosis strains have turned tuberculosis (TB) as "on the verge of eradication" to "most life threatening" disease. Furthermore, synergy with HIV and other immunosuppressive disease have strengthened its prevalence. This research reports small molecule anti-infectives which are specifically potent against several strains and isolates of TB. The hit compound 7f has also proved to be active against almost 25 clinical isolates comparable to marketed anti-TB agents.

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.

Synthesis of two 1,3,4-thiadiazole compounds: Crystal structure, theoretical and antifungal activity study

Two novel 1,3,4-thiadiazole compounds, C15H10N4S2 (5a) and C18H19N3S2 (5b) were designed and synthesized by reactions of key intermediate 5-(pyridin-4-yl)-1,3,4-thiadiazole-2-thiol and two substituted benzyl chloride (4-t-Bu and 3-CN). The two 1,3,4-thiadiazole structures were confirmed by 1H-NMR, MS , elemental analyses and X-Ray diffraction. Compound 5a is triclinic with space group P-1 and cell constants: A = 6.1426 (7), b = 8.5323 (14), c = 13.840 (2) ?, α = 90.199 (12), β = 90.002 (11), γ =106.762 (13)°, Dc = 1.484 g/cm3, Z = 2, V = 694.52 (17) ?3, the final R = 0.0400 and wR = 0.111 for 1786 observed reflections with I > 2σ(I). Compound 5b is triclinic with space group P2(1)/c and cell constants: A = 10.490 (5), b = 19.818 (10), c = 8.825(5) ?, α = 90, β = 98.989(10), γ =90°, Dc = 1.252 g/cm3, Z = 4, V = 1812.2(16) ?3, the final R = 0.0630 and wR = 0.192 for 2023 observed reflections with I > 2σ(I). Theoretical calculation was carried out by DFT method using 6-31G basis set. The compounds also possessed moderate fungicidal activity.

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.

Synthesis and antifungal activity of 1,3,4-thiadiazole derivatives containing pyridine group

Some 1,3,4-thiadiazole derivatives containing pyridine group were synthesized. The structures of 1,3,4-thiadiazoles were confirmed by 1H NMR, MS, and elemental analysis. The title compounds were investigated for antifungal activities. The results showed that some of them exhibited good antifungal activity.

Diaryl-Substituted Azolylthioacetamides: Inhibitor Discovery of New Delhi Metallo-β-Lactamase-1 (NDM-1)

The emergence and spread of antibiotic-resistant pathogens is a global public health problem. Metallo-β-lactamases (MβLs) such as New Delhi MβL-1 (NDM-1) are principle contributors to the emergence of resistance because of their ability to hydrolyze almost all known β-lactam antibiotics including penicillins, cephalosporins, and carbapenems. A clinical inhibitor of MBLs has not yet been found. In this study we developed eighteen new diaryl-substituted azolylthioacetamides and found all of them to be inhibitors of the MβL L1 from Stenotrophomonas maltophilia (KiiiII ion(s) preferentially via the triazole moiety, while other moieties interact mostly with the conserved active site residues Lys224 (CcrA, NDM-1, and ImiS) or Ser221 (L1).

Synthesis and evaluation of antimicrobial activity of some new hetaryl-azoles derivatives obtained from 2-aryl-4-methylthiazol-5- carbohydrazides and isonicotinic acid hydrazide

A series of new 1,3,4-oxadiazole/thiadiazole and 1,2,4-triazole derivatives have been synthesized starting from 2-aryl-4-methylthiazol-5-carbohydrazides and isonicotinic acid hydrazide. All the newly synthesized compounds were characterized by IR, 1

N-Heterocyclic dicarboxylic acids: Broad-spectrum inhibitors of metallo-β-lactamases with co-antibacterial effect against antibiotic-resistant bacteria

In an effort to identify novel, broad-spectrum inhibitors against the metallo-β-lactamases (MβLs), several N-heterocyclic derivatives were tested as inhibitors of MβLs CcrA, ImiS, and L1, which are representative enzymes from the distinct MβL subclasses. Three N-heterocyclic dicarboxylic acid derivatives were competitive inhibitors of CcrA and L1, exhibiting K i values ≤2 μM, while only 2,4-thiazolidinedicarboxylic acid (1b) was a competitive inhibitor of ImiS. Two 2-mercapto-1,3,4-thiadiazole derivatives were noncompetitive inhibitors of CcrA and ImiS, exhibiting K i values 7 μM; however, these same compounds did not inhibit L1. Two 2-mercapto-1,3,4-triazole derivatives were shown not to inhibit any of the tested MβLs. The N-heterocyclic derivatives were tested for antibacterial activity by examining the MIC values for existing antibiotics in the presence/absence of these derivatives. Consistent with the steady-state inhibition data, the inclusion of three N-heterocyclic dicarboxylic acid derivatives resulted in lower MIC values when using Escherichia coli BL21(DE3) cells containing the CcrA or L1 plasmids or Klebsiella pneumoniae (ATCC 700603), while 1b was the only dicarboxylic acid derivative to lower the MIC value of E. coli cells containing the ImiS plasmid. Inclusion of the 2-mercapto-1,3,4- thiadiazole derivatives resulted in lower MIC values for E. coli cells containing ImiS or L1 plasmids; however, these derivatives did not alter the MIC values for K. pneumoniae or E. coli cells containing the L1 plasmid. None of the N-heterocyclic derivatives affected the MIC of two methicillin resistant Staphylococcus aureus (MRSA) strains. Taken together, these studies demonstrate that N-heterocyclic dicarboxylic acids 1a-c and pyridylmercaptothiadiazoles 2a,b are good scaffolds for future broad-spectrum inhibitors of the MβLs.

Synthesis and biological activity test of some new five membered heterocycles

A new series of 1,3,4-oxadiazoles, 1,2,4-triazoles, 1,3,4-thiadiazoles were synthesized using alkylhydrazides as the starting materials, and then 1,2,4-triazoles were used to synthesize [1,2,4]triazolo[3,4-b][1,3,4] thiadiazoles. All the compounds were evaluated for in vitro antibacterial activity and antitumor activity. A new series of five membered heterocyclic compounds were synthesized using alkylhydrazides as the starting materials. All the compounds were evaluated for in vitro antibacterial activity and antitumor activity.

New potent inhibitors of tyrosinase: Novel clues to binding of 1,3,4-thiadiazole-2(3H)-thiones, 1,3,4-oxadiazole-2(3H)-thiones, 4-amino-1,2,4-triazole-5(4H)-thiones, and substituted hydrazides to the dicopper active site

A series of 1,3,4-thiadiazole-2(3H)-thiones, 1,3,4-oxadiazole-2(3H)-thiones, 4-amino-1,2,4-triazole-5(4H)-thiones, and substituted hydrazides were tailored and synthesized as new potent inhibitors of tyrosinase. The rationale for inhibitor design was based on the active site structural evidence from the crystal structures of bacterial tyrosinase and potato catechol oxidase enzymes. Kinetic and active site binding studies suggested mono-dentate binding of thiadiazole, oxadiazole, and triazole rings to the active site dicopper center of tyrosinase including hydrophobicity contributing to the potent inhibition. Kinetic plots showed mixed-type of inhibition by all 25 compounds. Substitutions at C3 of the triazole ring and C5 of the thiadiazole/oxadiazole rings were found to be playing a major role in the high binding affinity to tyrosinase. The current work may help develop new potent tyrosinase inhibitors against hyperpigmentation including potential insecticides.