- 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
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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.
- Hosseini, Saedehsadat,Esmaeili, Abbas Ali,Khojastehnezhad, Amir,Notash, Behrouz
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p. 628 - 644
(2021/07/02)
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- Synthesis and Biological Evaluation of Oxadiazole Clubbed Thiadiazole Derivatives as Antimicrobial Agents
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A series of 1,3,4-oxadiazole clubbed 1,3,4-thiadiazole derivatives were synthesized and assessed in vitro for their activity as antimicrobial agents. The target compounds 2-(5-(substituted aryl)-1, 3, 4-oxadiazol-2-ylthio)-N-(5-(substituted aryl)-1, 3, 4-thiadiazol-2-yl) acetamides (5a-5s) were synthesized using a basic condensation reaction between 5-(substituted aryl)-1,3,4-oxadiazole-2-thiol and 2-chloro-N-(5-(substituted aryl)-1,3,4-thiadiazol-2-yl)acetamide in presence of K2CO3 as a scavenging agent and acetone as reaction solvent. The titled compounds synthesized here, exhibited excellent to moderate antimicrobial activity against a broad panel of antibacterial strains of Gram-positive and Gram-negative bacteria and fungi.
- Begari, Eeshwaraiah,Dave, Alpa Y.,Joshi, Deepkumar S.,Parmar, Kokila A.
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p. 273 - 280
(2021/08/03)
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- Aryl or heteroaryl substituted thiadiazole compound and antibacterial application thereof
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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
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Paragraph 0095-0097; 0129-0130
(2021/01/30)
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- N-(5-phenyl-1, 3, 4-thiadiazole-2-yl) benzamide compound
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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.
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Paragraph 0051; 0057; 0090-0092
(2021/06/09)
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- N-thiadiazole-4-hydroxy-2-quinolone-3-carboxamides bearing heteroaromatic rings as novel antibacterial agents: Design, synthesis, biological evaluation and target identification
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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.
- Xue, Wenjie,Li, Xueyao,Ma, Guixing,Zhang, Hongmin,Chen, Ya,Kirchmair, Johannes,Xia, Jie,Wu, Song
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- Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies
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A series of 15 novel 1,3,4-thiadiazole amide derivatives containing a protocatechuic acid moiety were synthesized and structurally characterized. In addition, the corresponding imino (4) and amino (5) analogues of a phenyl-substituted 1,3,4-thiadiazole am
- Jakovljevi?, Katarina,Joksovi?, Milan D.,Botta, Bruno,Jovanovi?, Ljiljana S.,Avdovi?, Edina,Markovi?, Zoran,Mihailovi?, Vladimir,Andri?, Marijana,Trifunovi?, Sne?ana,Markovi?, Violeta
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p. 585 - 598
(2019/07/05)
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- Synthesis and molecular simulation study of furoic peptidomimetic derivatives as potent aminopeptodase N inhibitors
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The aminopeptidase N (APN) plays a critical role in angiogenesis and is over-expressed in tumor cells. In this paper, we report the synthesis and enzyme inhibition assay of furoic peptidomimetic compounds. These new compounds exhibit potent inhibitory ability toward APN with IC50 values lying in the micromolar level. The binding mode of inhibitors in APN active site was explained by a molecular simulation study. These data reveal that ligand coordinating with the catalytic Zn-ion is very important for inhibitory activities.
- Gao, Min,He, Junhua,Xu, Weidong,Lai, Xiaoping,Liu, Fen,Tu, Guogang
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p. 123 - 127
(2018/03/25)
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- Synthesis of matrinic amide derivatives containing 1,3,4-thiadiazole scaffold as insecticidal/acaricidal agents
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In continuation of our program aimed at the development of natural product-based pesticidal agents, a series of matrinic amide derivatives containing 1,3,4-thiadiazole scaffold were prepared, and their insecticidal and acaricidal activities were evaluated against Mythimna separata and Tetranychus cinnabarinus. Some compounds exhibited potent insecticidal and acaricidal activities. It suggested that R1 as a nitro group and R2 as a fluorine atom, were important for the insecticidal activity; R1 as the electron-donating groups and R2 as the methyl group, were necessary for the acaricidal activity.
- Lv, Min,Liu, Guangci,Jia, Minghong,Xu, Hui
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- PhI-Catalyzed Intramolecular Oxidative Coupling Toward Synthesis of 2-Amino-1,3,4-Thiadizoles
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A highly efficient method for the synthesis of thiadiazole derivatives via intramolecular oxidative coupling of thiosemicarbazide, using the in situ generated hypervalent iodine(III) reagents is developed. The protocol can be carried out smoothly and provides a variety of thiadiazole derivatives in moderate to excellent yields. Graphical Abstract: A highly efficient method for the synthesis of thiadiazole derivatives via PhI-catalyzed intramolecular oxidative coupling of thiosemicarbazide has been developed.
- Han, Yingzhi,Sun, Yadong,Abdukader, Ablimit,Liu, Bifu,Wang, Duozhi
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p. 3486 - 3491
(2018/09/27)
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- Synthesis and biological activity of acylthiourea derivatives contain 1,2,3-thiadiazole and 1,3,4-thiadiazole
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In order to investigate the biological activity of novel thiourea compounds, some novel 1,2,3-thiadiazole derivatives containing 1,3,4-thiadiazole were synthesized under phase transfer catalyzed condition(PEG-600)by multi-step reactions. The chemical structures of all compounds were established by 1H NMR, FTIR, MS, and elemental analysis, and some of these compounds were investigated for fungicidal activity and plant growth regulatory activity. The bioassay results indicated that some of these compound exhibited moderate activities.
- Yang, Ming-Yan,Zhao, Wen,Sun, Zhao-Hui,Tan, Cheng-Xia,Weng, Jian-Quan,Liu, Xing-Hai
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p. 314 - 318
(2015/04/14)
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- Design, synthesis and evaluation of small molecule imidazo[2,1-b][1,3,4]thiadiazoles as inhibitors of transforming growth factor-β type-I receptor kinase (ALK5)
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A new series of imidazo[2,1-b][1,3,4]thiadiazoles 5(a-g), 6(a-g), 9(a-i) and 12(a-h) were synthesized as transforming growth factor-β (TGF-β) type I receptor (also known as activin receptor-like kinase 5 or ALK5) inhibitors. These compounds were evaluated
- Patel, Harun M.,Sing, Baljeet,Bhardwaj, Varun,Palkar, Mahesh,Shaikh, Mahamadhanif S.,Rane, Rajesh,Alwan, Wesam S.,Gadad, Andanappa K.,Noolvi, Malleshappa N.,Karpoormath, Rajshekhar
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p. 599 - 613
(2015/03/18)
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- Synthesis of N-(5-aryl-1,3,4-thiadiazol-2-yl)-2-(3-oxo-1,2-benzothiazol- 2(3H)-yl)acetamide derivatives promoted by carbodiimide condensation
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Novel N-(5-aryl-1,3,4-thiadiazol-2-yl)-2-(3-oxo-1,2-benzothiazol-2(3H)-yl) acetamide derivatives were prepared by 1-(3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride and N-hydroxybenzotrizole condensation catalysis in a convenient and fast method
- Yu, Peng,Hu, Jun,Wan, Rong,Li, Xi,Zheng, Shanlong,Xu, Yanhua
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p. 347 - 350
(2014/07/08)
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- One-pot synthesis of 5H-1,3,4-thiadiazolo[3,2-a] pyrimidin-5-one derivatives
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A novel and efficient one-pot method has been developed for the synthesis of 2-substituted-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5- one derivative by the combination of [3 + 3] cycloaddition, reduction, deamination reactions. The fused heterocyclic compoun
- Dong, Hong-Ru,Gao, Zhong-Lian,Li, Rong-Shan,Hu, Yi-Ming,Dong, Heng-Shan,Xie, Zhi-Xiang
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p. 55827 - 55831
(2015/01/16)
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- An efficient synthesis of novel bis-1,3,4-thiadiazolyl-carbamate derivatives based on deoxycholic acid under microwave irradiation
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An easy and efficient method for the synthesis of novel deoxycholic acid bis-1,3,4-thiadiazol-carbamate derivatives under microwave irradiation has been developed. Twelve new methyl 3α,12α-bis-[(5-aryl-1,3,4-thiadiazol-2- yl) carbamoyloxy]-cholan-24-oates
- Zhao, Zhigang,Li, Lin,Liu, Min,Mei, Qinggang
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experimental part
p. 218 - 221
(2012/10/08)
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- Microwave-assisted synthesis of propesticides 1,3,4-thiadiazole aminophosphonates
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A novel and easy synthetic route to diethyl (5-substituted phenyl-1,3,4-thiadiazol-2-ylamino) (substituted phenyl) methylphosphonates has been achieved by the reaction of substituted benzylidene-5-(substituted phenyl)-1,3,4-thiadiazol-2-amines and diethyl phosphite under microwave irradiation. These 1,3,4-thiadiazole aminophosphonates were identified by infrared, 1H NMR, and elemental analyses. The target compounds were obtained in better yields (71-89%) and shorter time (10min) than with conventional heating.
- Wan, Rong,Wang, Peng,Han, Fen,Wang, Yao,Zhang, Jianqiang
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experimental part
p. 864 - 870
(2011/04/22)
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- Synthesis of some new triazole incorporated imidazo [2,1-b]-1,3,4- thiadiazoles
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A series of 6-[5-methyl-1 -(p-tolyl)-lH-1,2,3-triazol-4-yl]-2-substituted imidazo [2,1-b]-1,3,4-thiadiazoles 7 were synthesized by the reaction of 2-amino-5-substituted-1,3,4-thiadiazoles 6 with 2-bromo-1-[5-methyl-1-(p-tolyl)- 1H-1,2,3-triazol-4-yl] ethanone 4. Their structures were confirmed by 1H NMR, MS and IR spectra.
- Wang, Yan-Fei,Shen, Guo-Liang,Li, Rong-Shan,Dong, Heng-Shan
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p. 403 - 404
(2013/09/24)
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- Synthesis of 2-(N-formyl)-5-aryl/aryloxymethyl-1,3,4-thiadiazoles with potential bioactivity in PEG-400
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An environmental benign procedure for synthesis of 2-(N-formyl)-5-aryl/aryloxymethyl-1,3,4-thiadiazoles has been developed by reaction of 2-amino-5-aryl/aryloxymethyl-1,3,4-thiadiazoles with formic acid in PEG-400. The key advantages of this protocol are
- Wang, Xi Cun,Ding, Xiao Mei,Wang, Sheng Qing,Chen, Xue Fei,Quan, Zheng Jun
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scheme or table
p. 301 - 304
(2010/12/19)
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- Synthesis of 1,3,4-thiadiazole chrysanthemamide derivatives promoted by phenyldichlorophosphate catalysis
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A series of novel pro-pesticides with the activity of both 1,3,4-thiadiazole and chrysanthemic acid were synthesised using phenyldichlorophosphate catalysis. These 1,3,4-thiadiazole chrysanthemamides were identified by IR, 1H NMR and elemental
- Yu, Peng,Wan, Rong,Wang, Peng,Zhang, Jiang-Qiang,He, Qiu
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experimental part
p. 719 - 721
(2011/04/24)
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- Synthesis, antifungal activities and 3D-QSAR study of N-(5-substituted-1,3,4-thiadiazol-2-yl)cyclopropanecarboxamides
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A series of cyclopropanecarboxamide were prepared and tested for antifungal activity in vivo. The preliminary bioassays indicated that some compounds are comparable to the commercial fungicides. To further explore the comprehensive structure-activity relationship on the basis of fungicidal activity data, comparative molecular field analysis (CoMFA) was performed, and a statistically reliable model with good predictive power (r2 = 0.8, q2 = 0.516) was achieved. Based on the CoMFA, compound 7p was designed and synthesized, which was found to display a good antifungal activity (79.38%) as 7g and 7h.
- Liu, Xing-Hai,Shi, Yan-Xia,Ma, Yi,Zhang, Chuan-Yu,Dong, Wei-Li,Pan, Li,Wang, Bao-Lei,Li, Bao-Ju,Li, Zheng-Ming
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scheme or table
p. 2782 - 2786
(2009/10/19)
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- One pot synthesis of 1,3,4-thiadiazole thiazolidinone derivatives
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One pot synthesis of 2-(substitutedphenyl)-3-[5-(substitutedphenyl)-1,3,4- thiadiazol-2-yl]thiazolidin-4-one was developed by the reaction of 1,3,4-thiadiazole, substituted benzaldehyde and mercaptoacetic acid. These compounds were identified by IR,
- Wang, Peng,Wan, Rong,Han, Fen,Wang, Yao
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experimental part
p. 671 - 673
(2010/03/24)
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- Phase transfer catalysts promoting the one-pot synthesis under ultrasonic irradiation and biological activity of n-(5-substituted-1,3,4-thiadiazole-2-yl)- N'-(5-methylisoxazoyl)-thiourea derivatives
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Reaction of 2-amino-5-substitute-1,3,4-thiadiazoles with 5-methylisoxazoyl chloride and ammonium thiocyanate under the condition of solid-liquid phase-transfer catalysis using polyethylene glycol-600 (PEG-600) as the catalyst under ultrasonic irradiation yielded N-(5-substituted-1,3,4-thiadiazole-2-yl)- N'-(5-methylisoxazoyl)-thiourea derivatives 3a-1 in good-to-excellent yield. The chemical structure of all compounds was established by 1H NMR, FTIR, MS, and elemental analysis studies. Some of the compounds were investigated for fungicidal activity. The bioassay results indicated that some of these compounds exhibit moderate fungicidal activities.
- Xiaodong, Yang
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p. 387 - 392
(2008/09/19)
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- Heterocyclic systems containing bridgehead nitrogen atom: Reactions of 2-aminothiadiazoles with α-haloketones and ketones in presence of NBS
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Synthesis of 2,6-Diarylimidazo-1,3,4-thiadiazoles (III) have been achieved by the reaction of α-haloketones with 2-aminothiadiazoles (II) or more conveniently by treating II directly with ketones in the presence of NBS.Bromination of III furnishes
- Mohan, Jag,Anjaneyulu, G. S. R.,Kiran
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p. 500 - 502
(2007/10/02)
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- Antihypertensive Thiadiazoles. 1. Synthesis of Some 2-Aryl-5-hydrazino-1,3,4-thiadiazoles with Vasodilator Activity
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Some 2-Aryl-5-hydrazino-1,3,4-thiadiazoles have been synthesized and screened for antihypertensive activity.In general, compounds with a 2-substituted phenyl ring had higher activity than their 3- or 4-substituted counterparts or those containing heteroar
- Turner, Stephen,Myers, Malcolm,Gadie, Brian,Nelson, Anthony J.,Pape, Robin,et al.
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p. 902 - 906
(2007/10/02)
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- 1,4-Cycloaddition of Isothiocyanates to Azomethines and Fungitoxicity of Resulting 1,3,4-Thiadiazolo-s-triazine-5(6H,7H)-thiones
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Several 2,6,7-trisubstituted 1,3,4-thiadiazolo-s-triazine-5(6H,7H)-thiones have been prepared by 1,4-cycloaddition of aryl isothiocynates to 5-aryl(aryloxymethyl-2-benzylidene-amino-1,3,4-thiadiazoles (3a-e).The fungicidal activity of compounds has
- Singh, H.,Yadav, L. D. S.,Sharma, K. S.
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p. 480 - 481
(2007/10/02)
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- Synthesis and Antifungal Activity of Some 1,3,4-Thiadiazolo-s-triazine-7-thiones and N-Acyl-N'-(5-aralkyl/aryl-1,3,4-thiadiazol-2-yl)thioureas
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1-Acylthiosemicarbazides (1) on cyclodehydration with conc.H2SO4 give the corresponding 2-amino-5-aralkyl/aryl-1,3,4-thiadiazoles (2) which on treatment with acyl chlorides and NH4SCN in acetone followed by cyclisation of the resultant N-acyl-N'-(5-aralky
- Singh, S.,Yadav, L. D. S.,Singh, H.
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p. 518 - 520
(2007/10/02)
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