26907-54-0

Usage

Uses

Used in Organic Synthesis:
2-AMINO-5-(4-METHYLPHENYL)-1,3,4-THIADIAZOLE is used as a building block in organic synthesis for the creation of various compounds. Its unique structure and functional groups make it a versatile component in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-AMINO-5-(4-METHYLPHENYL)-1,3,4-THIADIAZOLE is used as a starting material for designing pharmaceutical agents. Its biological activities and chemical properties make it a promising candidate for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
2-AMINO-5-(4-METHYLPHENYL)-1,3,4-THIADIAZOLE is also utilized in the agrochemical industry as a starting material for the design of agrochemicals. Its potential biological activities can be harnessed to develop new pesticides, herbicides, or other agricultural chemicals to improve crop protection and yield.

InChI:InChI=1/C9H9N3S/c1-6-2-4-7(5-3-6)8-11-12-9(10)13-8/h2-5H,1H3,(H2,10,12)

Upstream product

• 43002-64-8 ethyl 4-methylbenzimidate hydrochloride 
• 79-19-6 thiosemicarbazide 
• 104-85-8 para-methylbenzonitrile 
• 104-87-0 4-methyl-benzaldehyde 
• 40739-81-9 p-tolualdehyde p-toluenesulfonylhydrazone 
• 333-20-0 potassium thioacyanate 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 3619-22-5 p-toluic hydrazide 
• 1079-82-9 C₉H₁₁N₃OS 
• 99-94-5 p-Toluic acid 
• 96134-00-8 C₁₁H₁₅N₃OS 
• 1079-82-9 1-(p-methylbenzoyl)-3-thisemicarbazide 
• 5706-83-2 4-methylbenzaldehyde thiosemicarbazone 

Downstream Products

• 59565-61-6 (4-nitro-benzylidene)-(5-p-tolyl-[1,3,4]thiadiazol-2-yl)-amine 
• 134839-40-0 N-(5-p-Tolyl-[1,3,4]thiadiazol-2-yl)-benzamidine 
• 134839-42-2 4-Chloro-N-(5-p-tolyl-[1,3,4]thiadiazol-2-yl)-benzamidine 
• 79225-84-6 N-(o-chlorobenzoyl)-N'-(5-p-tolyl-1,3,4-thiadiazol-2-yl)thiourea 
• 79225-89-1 1-[2-(4-Chloro-phenoxy)-acetyl]-3-(5-p-tolyl-[1,3,4]thiadiazol-2-yl)-thiourea 
• 100987-03-9 2-azido-5-(4-methylphenyl)-1,3,4-thiadiazole 
• 40288-18-4 2-chloro-5-(p-tolyl)-1,3,4-thiadiazole 
• 73653-70-0 6-phenyl-2-p-tolyl-imidazo[2,1-b][1,3,4]thiadiazole 
• 111750-57-3 2-chloro-N-[5-(4-methylphenyl)-[1,3,4]-thiadiazol-2-yl]-acetamide 
• 1073557-76-2 (2R)-N-[5-(4-methylphenyl)-1,3,4-thiadiazol-2-yl]-2-[(benzoyl)-amino]propanamide 
• 1073557-88-6 (2R)-N-[5-(4-methylphenyl)-1,3,4-thiadiazol-2-yl]-2-[(phenylacetyl)amino]propanamide 
• 1072008-43-5 (2R)-N-[5-(4-methylphenyl)-1,3,4-thiadiazol-2-yl]-2-[(phenylsulfonyl)amino]propanamide 
• 1186388-58-8 C₁₈H₁₅N₃O₃S 
• 1303531-61-4 C₁₉H₂₈N₄OS 

Relevant academic research and scientific papers

Aryl or heteroaryl substituted thiadiazole compound and antibacterial application thereof

The invention belongs to the technical field of medicines, and particularly relates to an aryl or heteroaryl substituted thiadiazole compound, a preparation method and application thereof as an antibacterial drug. The compound is represented by formula (1

N-(5-phenyl-1, 3, 4-thiadiazole-2-yl) benzamide compound

The invention belongs to the technical field of medicines, relates to a compound with antitumor activity and a specific chemical structure, and in particular relates to an N-((6, 7-dimethoxyquinoline-4-yl) oxy) methyl)-N-(5-phenyl-1, 3, 4-thiadiazole-2-yl) benzamide compound and a preparation method and an application thereof. The structural general formula of the compound is shown in the specification, wherein an R group is mono-substituted or double-substituted phenyl, fluorophenyl, chlorphenyl, bromophenyl, benzyl, benzyloxy, benzene nitro or trifluoromethyl substituted at 2-position, 3-position or 4-position. Pharmacological studies show that the compound provided by the invention has a relatively remarkable proliferation inhibition effect on HER-2 positive breast cancer cells SK-Br-3, the effect is obviously superior to that of HER-2 negative breast cancer cells MCF-7, the compound can be used for preparing antitumor drugs, and a new way is opened up for deep research and development of tumor drugs in the future. The preparation method provided by the invention is simple and feasible, relatively high in yield and easy for large-scale production.

Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from N-Tosylhydrazones

The diversity-oriented synthesis of 1,2,4-triazols, 1,3,4-thiadiazols, and 1,3,4-selenadiazoles from N-tosylhydrazones was developed, and the reactions were general for a wide range of substrates, in which NH2CN, KOCN, KSCN, and KSeCN were used as odorless sources. Two different pathways were proposed, and N-tosylhydrazonoyl chlorides were formed in situ in the presence of NCS.

An efficient synthesis of novel spiro[indole-3,8′-pyrano[2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidine derivatives via organobase-catalyzed three-component reaction of malononitrile, isatin and heterocyclic-1,3-diones

In this research, firstly, some derivatives of sulfur containing [1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one have been synthesized and then they were used for the synthesis of novel derivatives of 6′-amino-2,9′-dioxo-2′-phenyl-9′H-spiro[indoline-3,8′-pyrano[2,3-d][1,3,4]thiadiazolo[3,2-a]pyrimidine]-7′-carbonitriles via a one-pot three-component condensation reaction of 7-hydroxy-2-phenyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one derivatives, malononitrile and isatin compounds in the presence of DABCO as a organocatalyst and under solvent-free conditions. In this report, a new family of spiro-pyrano-thiadiazolo-pyrimidine derivatives have been synthesized in short reaction times (10–60 min) and good to excellent yields (80–96%). The structures of all synthesized products have been confirmed by IR, 1H NMR, 13C NMR and mass spectrometry, and the structure of one selected product was characterized by single-crystal X-ray diffraction studies as well.

Synthesis of Emodin Amide Derivatives Containing 1,3,4-Thiadiazole and Their Inhibitory Activity on Vibrio harveyi

A series of new 1,3,4-thiadiazole Emodin amide derivatives were synthesized through the connection of 5-substituted-1,3,4-thiadiazole-2-amine and Emodin carboxylic acids which were obtained by a two-step procedure starting from Emodin. Vibrio harveyi inhibition activities of the newly prepared compounds were evaluated. Results revealed that all compounds showed different degrees of inhibition on V. harveyi. Among them, compound 7a showed the best V. harveyi inhibition effect and the minimum inhibitory concentration (MIC) was 0.0625 mg/mL.

COMPOUNDS HAVING PDE9A INHIBITORY ACTIVITY, AND PHARMACEUTICAL USES THEREOF

The present invention provides a compound having a specific chemical structure and having PDE9A inhibitory activity, or a pharmaceutically acceptable salt thereof. The present invention provides a composition containing the compound or a pharmaceutically acceptable salt thereof. The present invention provides a pharmaceutical use, for treating or preventing PDE9A-related diseases, of the compound according to the present invention, a salt thereof, and a composition containing the compound or salt. The present invention also provides a method for treating or preventing PDE9A-related diseases, the method comprising administering an effective amount of the compound according to the present invention, a salt thereof, or a composition containing the compound or salt to a subject in need of treatment.

Gramine-based structure optimization to enhance anti-gastric cancer activity

Gramine is a natural indole alkaloid with a wide range of biological activities, but its anti-gastric cancer activity is poor. Herein, a pharmacophore fusion strategy was adopted to design and synthesize a new series of indole-azole hybrids on the structural basis of gramine. Based on our previous studies, different nitrogen-containing five-membered heterocyclic rings and terminal alkyne group were introduced into the indole-based scaffold to investigate their effect on improving the anti-gastric cancer activity of gramine derivatives. Structure-activity relationship (SAR) studies highlighted the role played by terminal alkyne in enhancing the inhibitory effect, and compound 16h displayed the best antiproliferative activity against gastric cancer MGC803 cells with IC50 value of 3.74 μM. Further investigations displayed compound 16h could induce mitochondria-mediated apoptosis, and caused cell cycle arrest at G2/M phase. Besides, compound 16h could inhibit the metastasis ability of MGC803 cells. Our studies may provide a new strategy for structural optimization of gramine to enhance anti-gastric cancer activity, and provide a potential candidate for the treatment of gastric cancer.

Design and development of 1,3,5-triazine-thiadiazole hybrids as potent adenosine A2A receptor (A2AR) antagonist for benefit in Parkinson's disease

Various studies showed adenosine A2A receptors (A2ARs) antagonists have profound therapeutic efficacy in Parkinsons Disease (PD) by improving dopamine transmission, thus being active in reversing motor deficits and extrapyramidal symptoms related to the disease. Therefore, in the presents study, we have showed the development of novel 1,3,5-triazine-thiadiazole derivative as potent A2ARs antagonist. In the radioligand binding assay, these molecules showed excellent binding affinity with A2AR compared to A1R, with significant selectivity. Results suggest, compound 7e as most potent antagonist of A2AR among the tested series. In docking analysis with A2AR protein model, compound 7e found to be deeply buried into the cavity of receptor lined via making numerous interatomic contacts with His264, Tyr271, His278, Glu169, Ala63, Val84, Ile274, Met270, Phe169. Collectively, our study demonstrated 1,3,5-triazine-thiadiazole hybrid as a highly effective scaffold for the design of new A2A antagonists.

N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides bearing heteroaromatic rings as novel antibacterial agents: Design, synthesis, biological evaluation and target identification

Due to the occurrence of antibiotic resistance, bacterial infectious diseases have become a serious threat to public health. To overcome antibiotic resistance, novel antibiotics are urgently needed. N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides are a potential new class of antibacterial agents, as one of its derivatives was identified as an antibacterial agent against S. aureus. However, no potency-directed structural optimization has been performed. In this study, we designed and synthesized 37 derivatives, and evaluated their antibacterial activity against S. aureus ATCC29213, which led to the identification of ten potent antibacterial agents with minimum inhibitory concentration (MIC) values below 1 μg/mL. Next, we performed bacterial growth inhibition assays against a panel of drug-resistant clinical isolates, including methicillin-resistant S. aureus, and cytotoxicity assays with HepG2 and HUVEC cells. One of the tested compounds named 1-ethyl-4-hydroxy-2-oxo-N-(5-(thiazol-2-yl)-1,3,4-thiadiazol-2-yl)-1,2-dihydroquinoline-3-carboxamide (g37) showed 2 to 128-times improvement compared with vancomycin in term of antibacterial potency against the tested strains (MICs: 0.25–1 μg/mL vs. 1–64 μg/mL) and an optimal selective toxicity (HepG2/MRSA, 110.6 to 221.2; HUVEC/MRSA, 77.6–155.2). Further, comprehensive evaluation indicated that g37 did not induce resistance development of MRSA over 20 passages, and it has been confirmed as a bactericidal, metabolically stable, orally active antibacterial agent. More importantly, we have identified the S. aureus DNA gyrase B as its potential target and proposed a potential binding mode by molecular docking. Taken together, the present work reports the most potent derivative of this chemical series (g37) and uncovers its potential target, which lays a solid foundation for further lead optimization facilitated by the structure-based drug design technique.

Synthesis, spectral characterization and DNA interactions of 5-(4-substituted phenyl)-1,3,4-thiadiazol-2-amine scaffolds

Five 5-(4-Substituted phenyl)-1, 3, 4-thiadiazole-2-amines have been prepared and structure of the compounds confirmed by spectroscopy studies. On the basis of spectroscopic studies, confirmed the formation of compounds. The DNA binding affinity of the prepared compounds was undertaken by absorption titration method and increasing the amount of CT-DNA observed hyperchromism or hypsochromism. The binding affinity compounds (except 5) are in the order of 4[13.341 × 104 M?1]>3 [8.505 × 104 M-1]>2 [3.567 × 104 M-1]>1[3.525 × 104 M?1]. The ethidiumbromide quenching results indicates CT-DNA was quenched by thiadiazoles via a static quenching mechanism. The DNA cleavage studies of the compounds were carried out in the presence and absence of H2O2 using gel electrophoresis experiment.