- The balance between hydrogen bonds, halogen bonds, and chalcogen bonds in the crystal structures of a series of 1,3,4-chalcogenadiazoles
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In order to explore how specific atom-to-atom replacements change the electrostatic potentials on 1,3,4-chalcogenadiazole derivatives, and to deliberately alter the balance between inter-molecular interactions, four target molecules were synthesized and characterized. DFT calculations indicated that the atom-to-atom substitution of Br with I, and S with Se enhanced the σ-hole potentials, thus increasing the structure directing ability of halogen bonds and chalcogen bonds as compared to intermolecular hydrogen bonding. The delicate balance between these intermolecular forces was further underlined by the formation of two polymorphs of 5-(4-iodophenyl)-1,3,4-thiadiazol-2-amine; Form I displayed all three interactions while Form II only showed hydrogen and chalcogen bonding. The results emphasize that the deliberate alterations of the electrostatic potential on polarizable atoms can cause specific and deliberate changes to the main synthons and subsequent assemblies in the structures of this family of compounds.
- Aaker?y, Christer B.,Averkiev, Boris B.,De Silva, Viraj,Sinha, Abhijeet S.
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Read Online
- Gramine-based structure optimization to enhance anti-gastric cancer activity
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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.
- Zhang, Xin-Hui,Guo, Qian,Wang, Heng-Ying,Li, Yi-Han,Khamis, Mussa Yussuf,Ma, Li-Ying,Wang, Bo,Liu, Hong-Min
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- Synthesis of Emodin Amide Derivatives Containing 1,3,4-Thiadiazole and Their Inhibitory Activity on Vibrio harveyi
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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.
- Cao, Lian-Gong,Cao, Zhi-Ling,Chen, Chao,Jiang, Kai-Jun,Liu, Shu-Hao,Liu, Wei-Wei,Ruan, Xin-Chi,Shao, Zhong-Bai,Shi, Da-Hua,Su, Zi-Qin,Wang, You-Xian,Wu, Yu-Ran,Wu, Yu-Yu
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p. 281 - 286
(2021/08/05)
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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; 0109-0110
(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; 0084-0086
(2021/06/09)
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- Further insight into the dual COX-2 and 15-LOX anti-inflammatory activity of 1,3,4-thiadiazole-thiazolidinone hybrids: The contribution of the substituents at 5th positions is size dependent
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Herin we report the design, synthesis, full characterization and biological investigation of new 15-LOX/COX dual inhibitors based on 1,3-thiazolidin-4-one (15-lipoxygenase pharmacophore) and 1,3,4-thiadiazole (COX pharmacophore) scaffolds. This series of molecular modifications is an extension of a previously reported series to further explore the structural activity relationship. Compounds 3a, 4e, 4n, 4q, 7 and 8 capable of inhibiting 15-LOX at (2.74, 4.2, 3.41, 10.21, 3.71 and 3.36 μM, respectively) and COX-2 at (0.32, 0.28, 0.28, 0.1, 0.28 and 0.27 μM, respectively). The results revealed that binding to 15-LOX and COX is sensitive to the bulkiness of the substituents at the 5 positions. 15-LOX bind better with small substituents, while COXs bind better with bulky substituents. Compounds 3a, 4r and 4q showed comparable in vivo anti-inflammatory activity to the reference drug (celecoxib). The ulcer liability test showed no sign of ulceration which ensures the safe gastric profile. Docking study was performed to explore the possible mode of interaction of the new compounds with the active site of human 15-LOX and COX-2. This study discloses some structural features for binding to 15-LOX and COX, thus pave the way to design anti-inflammatory agents with balanced dual inhibition of these enzymes.
- Abdel-Moty, Samia G.,Abdu-Allah, Hajjaj H. M.,Omar, Yasser M.
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- Synthesis of indole-tethered [1,3,4]thiadiazolo and [1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one hybrids as anti-pancreatic cancer agents
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New indole-tethered [1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one (8a-j) and [1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one hybrids (9a-e) were synthesized using [4+2] cycloaddition reactions of functionalized 1,3-diazabuta-1,3-dienes with indole-ketenes. All molecul
- Gummidi, Lalitha,Kerru, Nagaraju,Awolade, Paul,Raza, Asif,Sharma, Arun K.,Singh, Parvesh
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- Design and development of 1,3,5-triazine-thiadiazole hybrids as potent adenosine A2A receptor (A2AR) antagonist for benefit in Parkinson's disease
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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.
- Agnihotri, Amol Kumar,Bhat, Hans Raj,Giri, Sabeena,Masih, Anup,Pandey, Nidhi,Shrivastava, Jitendra Kumar,Singh, Saumya,Singh, Udaya Pratap
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- 1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure
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Three series of azo dyes derived from 2-amino-5-aryl-1,3,4-thiadiazoles and aniline, N,N-dimethylaniline and phenol were synthesized in high yields by a conventional diazotization-coupling sequence. The chemical structures of the prepared compounds were confirmed by 1H-NMR, 13C-NMR, IR, UV-Vis spectroscopy, mass spectrometry and elemental analysis. In addition, the X-ray single crystal structure of a representative azo dye was presented. For explicit determination of the influence of a substituent on radiation absorption in UV-Vis range, time-dependent density functional theory calculations were performed.
- Kudelko, Agnieszka,Olesiejuk, Monika,Luczynski, Marcin,Swiatkowski, Marcin,Sieranski, Tomasz,Kruszynski, Rafal
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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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- I2 Promoted Synthesis of 2-Aminothiadiazoles Employing KSCN as a Sulfur Source Under Metal-Free Conditions
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A new three-component strategy from aldehyde, p-toluenesulfonyl hydrazide and potassium thiocyanate for the synthesis of 2-aminothiadiazoles promoted by I2 under metal-free conditions has been described. Potassium thiocyanate was used as an odo
- Zhu, Fuyuan,Yan, Zhaohua,Ai, Chengmei,Wang, Yanmei,Lin, Sen
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supporting information
p. 6561 - 6565
(2019/10/22)
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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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- Cyclization–oxidation of Benzylidenehydrazinecarbothioamides by FeCl3.6H2O or ZnCl2.6H2O Catalysts and Synthesis of New 1,3,4-Thiadiazolo-[3,2- α]Pyrimidines
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We report new method for preparation of 2-amino-5-aryl-1,3,4-thiadiazoles by reaction of arylaldehyde with thiosemicarbazide and in the next step via cyclization of 2-aryl hydrazinecarbothioamide in the presence of ZnCl2.6H2O or FeCl3.6H2O. Also, in this research, new substituted 1,3,4-thiadiazolo-[3,2-α]pyrimidines were synthesized by the reaction of 2-amino-5-aryl-1,3,4-thiadiazoles derivatives with DMAD or DEAD in the presence of K2CO3 under reflux conditions. The FT-IR, 1H-NMR, 13C-NMR, elemental analysis and single- crystal X-ray analysis confirm the structures of the products.
- Darehkordi, Ali,Zarezadeh Abarqouei, Behnam,Rahmani, Fariba
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p. 1872 - 1879
(2017/05/29)
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- Thiadiazolodiazepine analogues as a new class of neuromuscular blocking agents: Synthesis, biological evaluation and molecular modeling study
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The synthesis, biological evaluation and molecular modeling study of 6,7-dihydro-[1,3,4] thiadiazolo[3,2-a][1,3]diazepine analogues as new class of neuromuscular blocking agents are described. The new compounds act via competitive mechanism with ACh which
- El-Subbagh, Hussein I.,El-Azab, Adel S.,Hassan, Ghada S.,El-Messery, Shahenda M.,Abdel-Aziz, Alaa A.-M.,El-Taher, Kamal E.H.
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- Synthesis, biological evaluation and molecular modeling study of thiadiazolo[3,2-a][1,3]diazepine analogues of HIE-124 as a new class of short acting hypnotics
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A new series of 6,7-dihydro-[1,3,4]thiadiazolo[3,2-a][1,3]diazepine analogues were synthesized, and biological evaluated. Compound GS-62 (33) exhibited potent in?vivo short acting hypnotic activity with onset time, duration of sleep and therapeutic index of 6.4?±?0.2, 94.8?±?5.3?min, 6.62, respectively), in comparison to thiopental sodium (6). Compounds 33 did not show any sign of acute tolerance reported with the maintenance dose of 6. Meanwhile 33 potentiated the in?vivo hypnotic effect of 6 in an equimolar amounts (0.06?mmol) combination showing an onset and duration of 7.5?±?1.3, 62.5?±?5.9?min, respectively. This combination allowed the use of lower doses of both drugs to avoid the undesirable side effects. Docking studies revealed favorable interactions and binding to BDZ binding site of the GABAAreceptor especially with Arg87, Arg149, and Thr151 amino acid residues.
- El-Subbagh, Hussein I.,Hassan, Ghada S.,El-Taher, Kamal E.H.,El-Messery, Shahenda M.,El-Azab, Adel S.,Abdelaziz, Alaa A.-M.,Hefnawy, Mohamed M.
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p. 237 - 247
(2016/09/09)
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- Synthesis and anti-inflammatory activity of some new thiadiazole linked pyrazole benzene sulphonamides as cyclooxygenase inhibitors
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A new series of thiadiazole linked pyrazole benzenesulfonamide derivatives were synthesized by the condensation of aldehydic pyrazole with aryl substituted thiadiazole amine followed by Schiff base reaction. The synthesized compounds (6a-o) were characterized by IR, NMR, and Mass spectral data, further evaluated their in-vivo anti-inflammatory, analgesic and invitro COX-II inhibition assay. The compounds 6b and 6m showed most significant in-vivo antiinflammatory with 72.33 &71.17% inhibition along analgesic activity having 67.89% and 71.37 % respectively. Their selectivity against COX-II enzyme with selectivity index 67.81 and 66.38 was established for 6b and 6m, which is compared with Celecoxib. During the gastric ulceration study, selected compounds couldn't observed any ulcerogenic effect on gastric mucosa. The in-silico pharmacokinetic profile and molecular docking study exposed very good binding affinity towards the Cyclooxygenase (COX-II) enzyme (PDB Id: 3PGH), therefore the compounds 6b and 6m are used as promising lead candidates for the support of drug development.
- Alam, Md. Jahangir,Alam, Ozair,Ali, Md. Rahmat,Naim, Mohd. Javed,Khan, Suroor Ahmad
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p. 1873 - 1885
(2016/02/27)
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- Photoredox catalysis of intramolecular cyclizations with a reusable silica-bound ruthenium complex
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Photoredox catalysis with the use of a stable, reusable silica-bound chromophore was applied to the intramolecular cyclization of a series of 2-benzylidenehydrazinecarbothioamides to give 5-phenyl-1,3,4-thiadiazol-2-amines. The catalyst was readily prepar
- Barbante, Gregory J.,Ashton, Trent D.,Doeven, Egan H.,Pfeffer, Frederick M.,Wilson, David J. D.,Henderson, Luke C.,Francis, Paul S.
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p. 1655 - 1658
(2015/06/08)
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- Improved antiproliferative activity of 1,3,4-thiadiazole-containing histone deacetylase (HDAC) inhibitors by introduction of the heteroaromatic surface recognition motif
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A series of 1,3,4-thiadiazole-containing hydroxamic acids, in accord with the common pharmacophore of histone deacetylase (HDAC) inhibitors (a Zn2+ binding moiety-a linker-a surface recognition motif), was identified as submicromolar HDAC inhibitors by our group. In this study, we continued our efforts to develop 1,3,4-thiadiazole bearing hydroxamate analogues by modifying the surface recognition motif. We found that 1,3,4-thiadiazoles having a heteroaromatic substituent showed better HDAC inhibitory activity in enzymatic assay and higher antiproliferative potency in cellular assay compared to SAHA.
- Guan, Peng,Wang, Lei,Hou, Xuben,Wan, Yichao,Xu, Wenfang,Tang, Weiping,Fang, Hao
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p. 5766 - 5775
(2015/02/02)
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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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- Synthesis, bioevaluation and docking study of 5-substitutedphenyl-1,3,4-thiadiazole-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents
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Since the first histone deacetylase (HDAC) inhibitor (Zolinza, widely known as suberoylanilide hydroxamic acid; SAHA) was approved by the Food and Drug Administration for the treatment of T-cell lymphoma in 2006, the search for newer HDAC inhibitors has attracted a great deal of interest of medicinal chemists worldwide. As a continuity of our ongoing research in this area, we designed and synthesized a series of 5-substitutedphenyl-1,3,4-thiadiazole-based hydroxamic acids as analogues of SAHA and evaluated their biological activities. A number of compounds in this series, for example, N1-hydroxy-N8-(5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl)octandiamide (5b), N1-hydroxy-N8-(5-(3-chlorophenyl-1,3,4-thiadiazol-2-yl)octandiamide (5c) and N1-hydroxy-N8-(5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl)octandiamide (5d), were found to possess potent anticancer cytotoxicity and HDAC inhibition effects. Compounds 5b-d were generally two- to five-fold more potent in terms of cytotoxicity compared to SAHA against five cancer cell lines tested. Docking studies revealed that these hydroxamic acid displayed higher affinities than SAHA toward HDAC8.
- Nam, Nguyen-Hai,Huong, Tran Lan,Dung, Do Thi Mai,Dung, Phan Thi Phuong,Oanh, Dao Thi Kim,Park, Sang Ho,Kim, Kyungrok,Han, Byung Woo,Yun, Jieun,Kang, Jong Soon,Kim, Youngsoo,Han, Sang-Bae
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p. 611 - 618
(2015/02/18)
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- Design of benzothiazole-1,3,4-thiadiazole conjugates: Synthesis and anticonvulsant evaluation
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Various 2-[(6-substituted-1,3-benzothiazol-2-yl)amino]-N-[5-substituted- phenyl-1,3,4-thiadiazol-2-yl]acetamides were synthesized with a prospective exploration of "lead hopping", using pharmacophoric elements for in vivo anticonvulsant activity. This yielded three potent candidates (5i, 5t, and 5u) in the preliminary screening employing the maximal electroshock seizure (MES) and the subcutaneous pentylenetetrazole (scPTZ) test, showing minimal neurotoxicity. Their quantitative study indicated an increase of nearly 2-10 times for the MES test and 7- to 67-fold for the scPTZ test in the protective index, the keystone in drug discovery for anticonvulsant activity. Various 2-[(6-substituted-1,3-benzothiazol-2-yl)amino]-N-[5-substituted-phenyl-1,3, 4-thiadiazol-2-yl]acetamides were synthesized with a prospective exploration of "lead hopping", using pharmacophoric elements for in vivo anticonvulsant activity. Three potent candidates (5i, 5t, and 5u) with minimal neurotoxicity were identified in the MES and scPTZ tests.
- Siddiqui, Nadeem,Ahuja, Priya,Malik, Sachin,Arya, Satish K.
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p. 819 - 831
(2013/12/04)
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- New thiazolidinedione-5-acetic acid amide derivatives: Synthesis, characterization and investigation of antimicrobial and cytotoxic properties
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The present work describes the synthesis, antimicrobial and cytotoxic activity of 2,4-thiazolidinedione- 5-acetic acid amides 3a-n. The structures of the compounds were confirmed by IR, 1H, 13C NMR and elemental analysis. All compounds were tested for antimicrobial activity by twofold serial dilution technique. The preliminary results revealed that the compound 3d exhibits promising antibacterial and antifungal activity. The cytotoxic (MTT) activity of 2,4-thiazolidinedione-5-acetic acid amides were tested in four tumour cell lines. We found that compound 3j inhibited proliferation of HeLa, HT29, A549 and MCF-7 cell lines with IC50 values of 33, 35, 30 and 36 μM, respectively. Springer Science+Business Media, LLC 2011.
- Alegaon, Shankar G.,Alagawadi, Kallanagouda R.
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experimental part
p. 816 - 824
(2012/10/07)
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- Synthesis, biological evaluation, and molecular docking studies of cinnamic acyl 1,3,4-thiadiazole amide derivatives as novel antitubulin agents
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A series of cinnamic acyl 1,3,4-thiadiazole amide derivatives (6a-10e) have been designed and synthesized, and their biological activities were also evaluated as potential antiproliferation and tubulin polymerization inhibitors. Among all the compounds, 10e showed the most potent activity in vitro, which inhibited the growth of MCF-7 and A549 cell lines with IC50 values of 0.28 and 0.52 μg/mL, respectively. Compound 10e also exhibited significant tubulin polymerization inhibitory activity (IC50 = 1.16 μg/mL). Docking simulation was performed to insert compound 10e into the crystal structure of tubulin at colchicine binding site to determine the probable binding model. Based on the preliminary results, compound 10e with potent inhibitory activity in tumor growth may be a potential anticancer agent.
- Yang, Xian-Hui,Wen, Qing,Zhao, Ting-Ting,Sun, Jian,Li, Xi,Xing, Man,Lu, Xiang,Zhu, Hai-Liang
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experimental part
p. 1181 - 1187
(2012/03/26)
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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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- Thiadiazole derivatives as potential anticonvulsant agents
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A series of thiadiazole derivatives were synthesized with differently substituted benzoic acids which were cyclized to give differently substituted thiazolidin-4-one. Elemental analysis, IR,1HNMR,13C NMR and mass spectral data confir
- Mullick, Pooja,Khan, Suroor A.,Verma, Surajpal,Alam, Ozair
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experimental part
p. 1011 - 1016
(2012/01/03)
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- Microwave-assisted synthesis of 1,3,4-thiadiazole Schiff base derivatives
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A rapid and efficient microwave-assisted synthesis method for the preparation of 1,3,4-thiadiazole Schiff base derivatives is described. These 1,3,4-thiadiazole Schiff bases (5a-h) were identified by IR, 1H NMR, elemental analyses. The target c
- Hu, Jun,Sun, Jianguang,Zhou, Taoyu,Xu, Yanhua
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experimental part
p. 442 - 443
(2011/11/06)
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- Synthesis and antimicrobial evaluation of 5-(p-substituted phenyl)-N-(3-(5-nitrofur-2-yl) allylidene)-1,3,4-thiadiazol-2-amine derivatives
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5-(p-Substituted phenyl)-N-(3-(5-nitrofur-2-yl)allylidene)-1,3,4- thiadiazol-2-amines 10-17 were prepared utilizing different p-substituted benzoic acid through two step reactions. Firstly, thiosemicarbzide was reacted with benzoic acid derivatives 1 in t
- Salih, Nadia,Salimon, Jumat,Yousif, Emad
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experimental part
p. 373 - 383
(2012/04/04)
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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-salicylidene-5-(substituted)-1,3,4-thiadiazole as potential antimicrobial agents
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Several new 2,5-disubstituted derivatives of 1,3,4-thiadiazoles containing imine moiety were obtained from cyclization of thiosemicarbazide and corresponding p-substituted carboxylic acid in phosphorus oxychloride then the resulted products were reacted w
- Salimon, Jumat,Salih, Nadia,Ibraheem, Hanan,Yousif, Emad
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experimental part
p. 5289 - 5296
(2012/07/28)
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- Synthesis, characterization and antimicrobial activity of new thiadiazole derivatives
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A series of thiadiazole derivatives were synthesized with differently substituted benzoic acids which were cyclized to give differently substituted thiazolidin-4-one. Elemental analysis, IR, 1H NMR, 13C NMR and mass spectral data confirmed the
- Mullick, Pooja,Khan, Suroor A.,Verma, Surajpal,Alam, Ozair
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experimental part
p. 2345 - 2350
(2010/11/16)
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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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- Novel aminopeptidase N inhibitors derived from 1,3,4-thiadiazole scaffold
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The aminopeptidase N (APN/CD13), overexpressed in tumor cells, plays a critical role in angiogenesis. In this study, we report the synthesis and in vitro enzyme inhibition assay of 1,3,4-thiadiazole scaffold compounds. These new compounds have potent inhi
- Tu, GuoGang,Li, ShaoHua,Huang, HuiMing,Li, Gang,Xiong, Fang,Mai, Xi,Zhu, HuaWei,Kuang, BinHai,Xu, Wen Fang
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p. 6663 - 6668
(2008/12/22)
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