726-25-0Relevant articles and documents
Small molecule recognition of mephedrone using an anthracene molecular clip
Kellett, Kathryn,Broome, J. Hugh,Zloh, Mire,Kirton, Stewart B.,Fergus, Suzanne,Gerhard, Ute,Stair, Jacqueline L.,Wallace, Karl J.
, p. 7474 - 7477 (2016)
An anthracene molecular probe has been synthesised and shown to target mephedrone, a stimulant drug from the cathinone class of new psychoactive substances (NPS). A protocol has been developed to detect mephedrone via the probe using NMR spectroscopy in a
Synthesis, crystal structure, anticancer and molecular docking studies of quinolinone-thiazolidinone hybrid molecules
Krishnappagowda, Lokanath Neratur,Kumar, Vasantha,Pai, Vinitha R.,Poojary, Boja,Rai, Vaishali M.,Shivalingegowda, Naveen,Udupi, Vishwanatha
, (2021/08/12)
A new series of quinolone-thiazolidinone hybrid molecules 8a-o were prepared. Quinoline compounds were synthesized by Meth-Cohn synthesis and were condensed with 2,3-disubstituted thiazolidinone. These molecules were screened for their anticancer activities against MDA-MB-231 and MCF-7 cell line using MTT assay. Potent compounds were tested for their cytotoxicity on normal HEK 293 cell lines and most potent compound was tested for its cell cycle analysis. Molecular docking and molecular dynamic studies were performed on human N-acetyl transferase (hNAT-1) protein using Schrodinger molecular docking toolkit. Compound 8n emerged as potent with IC50 8.16?μM against MDA-MB-231 cell line followed by 8e with IC50 17.68?μM. Compound 8n arrested cell cycle at G2/M phase and was non-toxic to human normal kidney cell line. The potent compound 8n binds well with human NAT-1 protein with remarkable hydrogen bonding and π–π interactions. Molecular dynamic studies of 8n further confirm the target for these molecules. Target quinolinone-thiazolidinones were found to be new class of compounds targeting hNAT-1 and can serve as new lead compounds in drug discovery.
Preparation method of thiourea alkylation derivative
-
Paragraph 0037-0044, (2021/03/31)
The invention discloses a preparation method of a thiourea alkylation derivative, which comprises the following steps: stirring an aldehyde, N-arylthiourea, trichlorosilane and Lewis base in an organic solvent at a range of -10 DEG C to room temperature for reaction, and carrying out after-treatment to obtain the thiourea alkylation derivative, wherein the molar ratio of the aldehyde to the N-arylthiourea is 1:2 to 2:1, the molar ratio of the aldehyde to the Lewis base is 1:(0.01-0.20), the molar ratio of the aldehyde to trichlorosilane is 1:(1-2), R1 is a C1-C5 saturated alkyl group, or an unsubstituted or substituted aromatic ring, and R2 is H, an electron withdrawing substituent or an electron donating substituent. According to the method, trichlorosilane is catalyzed by the micromolecular Lewis base, reductive alkylation of thiourea is realized, synthesis can be realized by a one-pot method, and the method is simple to operate, short in reaction time, low in substrate toxicity, lowin cost, easy to obtain, mild in reaction condition and high in safety.
Hydroamination of isocyanates and isothiocyanates by alkaline earth metal initiators supported by a bulky iminopyrrolyl ligand
Bano, Kulsum,Anga, Srinivas,Jain, Archana,Nayek, Hari Pada,Panda, Tarun K.
supporting information, p. 9419 - 9428 (2020/06/17)
A series of new heteroleptic alkaline earth (Ae) metal complexes of general formula [{(Ph2CHN-CH)2C4H2N}AeI(THF)3] {Ae = Ca (2), Sr (3), and Ba (4)} were synthesizedviasalt metathesis by reacting potassium salt of ligand1-K[{(Ph2CHN-CH)2C4H2N}K(THF)2] with anhydrous alkaline earth metal diiodides (AeI2). The homoleptic calcium and barium complexes [{(Ph2CHN-CH)2C4H2N}2Ae] [Ae = Ca (5), Ba (6)] were prepared by treating metal bis-hexamethyldisilazide [Ae{N(SiMe3)2}2(THF)2] with the protic ligand1-H[(Ph2CH-N-CH)2C4H2NH] in a 1:2 molar ratio. Calcium complex5was used as an active pre-catalyst for the addition of N-H bond of arylamines across the heterocumulenes such as phenylisocyanate (PhNCO) and phenylisothiocyanate (PhNCS) under neat conditions, and up to 99% yields of the corresponding urea and thiourea derivatives were obtained.
Hydrogen-Bond Catalysis of Imine Exchange in Dynamic Covalent Systems
Schaufelberger, Fredrik,Seigel, Karolina,Ramstr?m, Olof
supporting information, p. 15581 - 15588 (2020/10/02)
The reversibility of imine bonds has been exploited to great effect in the field of dynamic covalent chemistry, with applications such as preparation of functional systems, dynamic materials, molecular machines, and covalent organic frameworks. However, acid catalysis is commonly needed for efficient equilibration of imine mixtures. Herein, it is demonstrated that hydrogen bond donors such as thioureas and squaramides can catalyze the equilibration of dynamic imine systems under unprecedentedly mild conditions. Catalysis occurs in a range of solvents and in the presence of many sensitive additives, showing moderate to good rate accelerations for both imine metathesis and transimination with amines, hydrazines, and hydroxylamines. Furthermore, the catalyst proved simple to immobilize, introducing both reusability and extended control of the equilibration process.
Development of phenylthiourea derivatives as allosteric inhibitors of pyoverdine maturation enzyme PvdP tyrosinase
Dekker, Frank J.,Quax, Wim J.,Voet, Julian M.,Wibowo, Joko P.,Xiao, Zhangping
supporting information, (2020/07/21)
Infections caused by Pseudomonas aeruginosa become increasingly difficult to treat because these bacteria have acquired various mechanisms for antibiotic resistance, which creates the need for mechanistically novel antibiotics. Such antibiotics might be developed by targeting enzymes involved in the iron uptake mechanism because iron is essential for bacterial survival. For P. aeruginosa, pyoverdine has been described as an important virulence factor that plays a key role in iron uptake. Therefore, inhibition of enzymes involved in the pyoverdine synthesis, such as PvdP tyrosinase, can open a new window for the treatment of P. aeruginosa infections. Previously, we reported phenylthiourea as the first allosteric inhibitor of PvdP tyrosinase with high micromolar potency. In this report, we explored structure-activity relationships (SAR) for PvdP tyrosinase inhibition by phenylthiourea derivatives. This enables identification of a phenylthiourea derivative (3c) with a potency in the submicromolar range (IC50 = 0.57 + 0.05 μM). Binding could be rationalized by molecular docking simulation and 3c was proved to inhibit the bacterial pyoverdine production and bacterial growth in P. aeruginosa PA01 cultures.
Facile synthesis of phthalidyl fused spiro thiohydantoins through silica sulfuric acid induced oxidative rearrangement of ninhydrin adducts of thioureas
Mandal, Subhro,Pramanik, Animesh
, (2019/12/24)
A one-pot three-component sequential synthetic protocol produces structurally and biologically important phthalidyl fused spiro N,N′-disubstituted thiohydantoins from readily available aromatic isothiocyanates, primary amines and ninhydrin. In this three-step synthesis while the initial two steps are catalyst-free, in the final step silica sulfuric acid (SSA) induces an oxidative rearrangement in [3.3.0]-bicyclic 1,2-diol adducts of ninhydrin and thioureas under solvent-free condition to generate the final products spiro-fused thiohydantoins. The adequate acidity of SSA in cooperation with moderate oxidizing property promotes a facile oxidative rearrangement in 1,2-diol intermediates to produce the spiro-fused thiohydantoins with diverse functionalities. Easy recyclability of SSA, good to excellent yield of the products, wider substrate scope, shorter reaction time, solvent-free two steps out of three and high atom economy make this method attractive and practicable.
Synthesis of metronidazole based thiazolidinone analogs as promising antiamoebic agents
Ansari, Mohammad Fawad,Inam, Afreen,Ahmad, Kamal,Fatima, Shehnaz,Agarwal, Subhash M.,Azam, Amir
supporting information, (2020/10/12)
Metronidazole and its derivatives are widely used for the treatment of amoebiasis. However, metronidazole is considered as the standard drug but it has many side effects. The present study describes the synthesis of a series of metronidazole based thiazolidinone analogs via Knoevenagel condensation of 4-[2-(2-methyl-5-nitro-1H-imidazole-1-yl)ethoxy]benzaldehyde 1 with various thiazolidinone derivatives 2–14 to get the new scaffold (15–27) having better activity and lesser toxicity. Six compounds have shown better efficacy and lesser cytotoxicity than the standard drug metronidazole towards HM1: IMSS strain of Entamoeba histolytica. These compounds may combat the problem of drug resistance and might be effective in identifying potential alternatives for future drug discovery against EhOASS.
Micelle-Enabled One-Pot Guanidine Synthesis in Water Directly from Isothiocyanate using Hypervalent Iodine(III) Reagents under Mild Conditions
Srisa, Jakkrit,Tankam, Theeranon,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit
, p. 3335 - 3343 (2019/09/12)
In this work, we developed a one-pot synthesis of guanidine directly from isothiocyanate using DIB (diacetoxyiodobenzene) as a desulfurizing agent under micellar conditions in water. Our optimization study revealed that the use of 1 % TPGS-750-M as a surfactant with NaOH as an additive base at room temperature can convert a variety of isothiocyanates and amines into corresponding guanidines in excellent yields (69–95 %). This synthetic process in water can be applied to prepare guanidine at gram-scale quantity. Our aqueous micellar medium also demonstrated high reusability as the reaction can be performed for several cycles without losing its efficiency. The reaction is metal-free, utilizes water as solvent and practical (room temperature and open flask).
One-step construction of unsymmetrical thioureas and oxazolidinethiones from amines and carbon disulfide: Via a cascade reaction sequence
Ding, Chaochao,Wang, Shaoli,Sheng, Yaoguang,Dai, Qian,Zhao, Yunjie,Liang, Guang,Song, Zengqiang
, p. 26768 - 26772 (2019/09/06)
A concise and versatile method for the construction of unsymmetrical thioureas and oxazolidinethiones from amines and carbon disulfide has been achieved in DMSO without addition of extra reagents. The present protocol is compatible with various secondary amines and primary amines, and suitable for intermolecular and intramolecular reactions. Diverse unsymmetrical thioureas and oxazolidinethiones were efficiently obtained in good to excellent yields via a cascade reaction sequence.
