- Synthesis and evaluation of the anticancer activity of [Pt(diimine)(N,N-dibutyl-N′-acylthiourea)]+complexes
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Despite the concerted efforts to develop targeted cancer treatments, these therapies are plagued by the rapid development of resistance and serious adverse drug reactions. Based on the wide clinical use and successes of the platinum drugs like cisplatin and oxaliplatin, we investigated the synthesis and potential anticancer efficacy of alternative platinum complexes. A series of nine cationic square planar platinum(ii) complexes were synthesized and characterized and then evaluated for their anticancer activity. The complexes were of the type [Pt(diimine)(Ln-κO,S)]+where diimine is either 1,10-phenanthroline (phen), 5,6-dimethyl-1,10-phenanthroline (dmp) or dipyrido[3,2-f:2′,3′-h]quinoxaline (dpq) and Ln-κO,Srepresenting variousN,N-dibutyl-N′-acylthiourea ligands. The anticancer activity of the synthesised complexes was evaluated against two lung cancer cell lines (A549 and H1975) and a colorectal cancer cell line, HT-29. The 50% inhibitory concentrations (IC50) for the most cytotoxic compounds were determined and the mode of cell death evaluated. The structure-activity relationships indicated that complexes with the 5,6-dimethyl-1,10-phenanthroline variation of the diimine ligand were the most active against the cell lines tested, while the activity of complexes based on the acylthiourea ligand varied between the cell lines. IC50values for the three active platinum complexes were in the low micromolar range for the three cell lines and ranged between 0.68 μM and 2.28 μM. Changes to cell morphology indicate that the active platinum complexes induce cell death by both apoptosis and paraptosis. The complexes were able to induce the nuclear expression of the cyclin-dependent kinase inhibitor, p21, which is an indicator of DNA damage. The collective data indicate that these platinum complexes are valuable lead compounds for further analysis and cancer drug discovery.
- Peega, Tebogo,Magwaza, Rachael N.,Harmse, Leonie,Kotzé, Izak A.
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p. 11742 - 11762
(2021/09/06)
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- 1,2,4-Thiadiazole acyclic nucleoside phosphonates as inhibitors of cysteine dependent enzymes cathepsin K and GSK-3β
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In analogy to antiviral acyclic nucleoside phosphonates, a series of 5-amino-3-oxo-1,2,4-thiadiazol-3(2H)-ones bearing a 2-phosphonomethoxyethyl (PME) or 3-hydroxy-2-(phosphonomethoxy)propyl (HPMP) group at the position 2 of the heterocyclic moiety has be
- Pomeislová, Alice,Otmar, Miroslav,Rube?ová, Petra,Beny?ek, Jakub,Matou?ová, Marika,Mertlíková-Kaiserová, Helena,Pohl, Radek,Po?tová Slavětínská, Lenka,Pomeisl, Karel,Kre?merová, Marcela
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- Impact of aliphatic acyl and aromatic thioamide substituents on the anticancer activity of Ru(ii)-: P -cymene complexes with acylthiourea ligands - In vitro and in vivo studies
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Six different acylthiourea ligands (L1-L6) and their corresponding Ru(ii)-p-cymene complexes (P1-P6) were designed to explore the structure-activity relationship of the complexes upon aliphatic chain and aromatic conjugation on the C- and N-terminals, res
- Balakrishnan, Nithya,Bhuvanesh, Nattamai,Echeverria, Cesar,Gayathri, Dasararaju,Haribabu, Jebiti,Karvembu, Ramasamy,Mohamed Subarkhan, Mohamed Kasim,Swaminathan, Srividya
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p. 16311 - 16325
(2021/11/27)
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- Design, Synthesis, and Insecticidal Activity of Novel Doramectin Derivatives Containing Acylurea and Acylthiourea Based on Hydrogen Bonding
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Our recent investigation on the insecticidal activities of several doramectin derivatives preliminarily revealed that the presence of hydrogen bonds at the C4″ position of the molecule with target protein γ-aminobutyric acid (GABA) receptor was crucial for retaining high insecticidal activity. As a continuation of our research work on the development of new insecticides, two series of novel acylurea and acylthiourea doramectin derivatives were designed and synthesized. The bioassay results indicated that the newly synthesized compounds (5o, 5t, and 6t) exhibited higher insecticidal activity against diamondback moth, oriental armyworm, and corn borer than the control compounds doramectin, commercial avermectins, chlorbenzuron, and lead compound 3g in our laboratory. Specifically, compound 5t was identified as the most promising insecticide against diamondback moth, with a final mortality rate of 80.00% at the low concentration of 12.50 mg/L, showing approximately 7.75-fold higher potency than the parent doramectin (LC50 value of 48.1547 mg/L), 6.52-fold higher potency than commercial avermectins (LC50 value of 40.5507 mg/L), and 3.98-fold higher potency than compound 3g (LC50 value of 24.7742 mg/L). Additionally, molecular docking simulations revealed that compound 5t (2.17, 2.20, 2.56, and 2.83 ?) displayed stronger hydrogen-bond action in binding with the GABA receptor, better than that of compound 5o (1.64 and 2.15 ?) and compound 6t (2.20 and 2.31 ?) at the C4″ position. This work demonstrated that these compounds containing hydrogen-bond groups might contribute to the improvement of insecticidal activity and supply certain hints toward structure optimization design for the development of new insecticides.
- Bai, Ping,Cheng, Yao,Lu, Xiaoxia,Yang, Jian,Zhang, Qi,Zheng, Cheng
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p. 5806 - 5815
(2020/06/19)
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- Design, green synthesis, molecular docking and anticancer evaluations of diazepam bearing sulfonamide moieties as VEGFR-2 inhibitors
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Novel series of diazepam bearing sulfonamide moieties 5a-f and 7a-c were designed, synthesized and evaluated for anticancer activity against HepG2, HCT-116 and MCF-7 cell lines. MCF-7 was the most sensitive cell line to the influence
- Saleh, Nashwa M.,El-Gaby, Mohamed S.A.,El‐Adl, Khaled,Abd El-Sattar, Nour E.A.
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- Synthesis, inhibition studies against AChE and BChE, drug-like profiling, kinetic analysis and molecular docking studies of N-(4-phenyl-3-aroyl-2(3H)-ylidene) substituted acetamides
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Halogenated and non-halogenated N-(4-phenyl-3-aroyl-2(3H)-ylidene) substituted acetamides were prepared by base-catalyzed cyclization of corresponding acetyl thioureas with phenacyl bromide. The synthesized compounds were structurally characterized by 1H NMR and 13C NMR spectroscopy and were screened against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzyme inhibition activities. Molecular docking studies, drug-like profiling and kinetic analysis were performed to further investigate the inhibition mechanism of the compounds. This study provided useful insights into the design and development of novel dual inhibitors, in addition to understanding the mechanism by which such drugs interact with targets and exert their biochemical action. All the compounds showed superior inhibition profile compared to the standards possessing sub-micromolar and micromolar IC50 values for AChE and BChE, respectively. Docking simulations revealed that the compound 6g showed strong binding inside the active site gorges of both AChE and BChE. An excellent agreement was obtained as the best docked poses showed important binding features mostly based on interactions due to aromatic moieties and oxygen atoms of the compound. Cation-pi/pi-pi interactions together with hydrogen bond forces were the key players responsible for ligand anchoring in the active sites. The striking results accomplished both in docking computations and experimental findings ascertained that the compound 6g can serve as a scaffold for both AChE and BChE inhibition.
- Larik, Fayaz Ali,Saeed, Aamer,Faisal, Muhammad,Hamdani, Salma,Jabeen, Farukh,Channar, Pervaiz Ali,Mumtaz, Amara,Khan, Imtiaz,Kazi, Mahar Ali,Abbas, Qamar,Hassan, Mubashir,Korabecny, Jan,Seo, Sung-Yum
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- Novel N-(benzo[d]oxazol-2-yl)alkanamides; synthesis and carbonic anhydrase II inhibition studies
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Carbonic anhydrase (CA II) inhibitors are very important therapeutic targets in drug design for treatment of neuropathic pain and in eradication of glaucoma, cancer, epilepsy, ulcer and obesity. In this study, some two2-substituted benzoxazoles (3a-j) wer
- Saeed, Aamer,Channar, Pervaiz A.,Arshad, Muhammad,El-Seedi, Hesham R.,Abbas, Qamar,Hassan, Mubashir,Raza, Hussain,Seo, Sung-Yum
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p. 2831 - 2843
(2020/05/25)
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- 3-Aminobenzenesulfonamides incorporating acylthiourea moieties selectively inhibit the tumor-associated carbonic anhydrase isoform IX over the off-target isoforms I, II and IV
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We describe the synthesis of a series of novel 1-aroyl/acyl-3-(3-aminosulfonylphenyl) thioureas (4a–k) acting as human carbonic anhydrase (hCA, EC 4.2.1.1) inhibitors. Reaction of alkyl/aryl isothiocyanates with 3-aminobenzenesulfonamide afforded a series of the title compounds incorporating a variety of short as well as highly lipophilic long tails. The newly synthesized sulfonamides were evaluated against 4 physiologically relevant CA isoforms (hCA I, II, IV, and IX). Several compounds showed interesting inhibitory activity. The tumor-associated hCA IX was the most sensitive isoform to inhibition with these compounds, with KIs in the range of 21.5–44.0 nM and selectivity ratios over the major cytosolic isoform hCA II in the range of 3.35–37.3. The sulfonamides incorporating the phenylacetylthioureido and pentadecanoylthioureido moieties were the most hCA IX-selective inhibitors detected in this work, making them of interest for further investigations.
- Fattah, Tanzeela Abdul,Bua, Silvia,Saeed, Aamer,Shabir, Ghulam,Supuran, Claudiu T.
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p. 123 - 128
(2018/10/20)
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- Synthesis, Characterization, and Computional Studies of Triazatetracyclo Acetamide
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N-[(9E)-8,0 10,0 17-triazatetracyclo[8.7.0.02,7.011,18]heptadeca-1(17),2(7),3,5,11,13,15-heptaen-9-ylidene] acetamide (I) is synthesized and characterized by spectroscopy, microanalysis, and single crystal X-ray diffractometry. Compound 1 crystallizes in the monoclinic space group P21/n with a = 17.5552(17) ?, b = 4.6163(4) ?, c = 17.7662(17) ?, β = 115.953(3)°, and Z = 4. The bond angles and bond lengths of the compound are computed using the density functional theory with B3LYP, BPW91, and wB97XD functionals and the 6-31G++(d,p) basis set. The frontier orbitals that contribute to the reactivity of triazatetracyclics are discussed.
- Odame,Hosten,Tshentu
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p. 1804 - 1809
(2019/01/14)
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- Synthesis of sulfadiazinyl acyl/aryl thiourea derivatives as calf intestinal alkaline phosphatase inhibitors, pharmacokinetic properties, lead optimization, Lineweaver-Burk plot evaluation and binding analysis
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To seek the new medicinal potential of sulfadiazine drug, the free amino group of sulfadiazine was exploited to obtain acyl/aryl thioureas using simple and straightforward protocol. Acyl/aryl thioureas are well recognized bioactive pharmacophore containin
- Sajid-ur-Rehman,Saeed, Aamer,Saddique, Gufran,Ali Channar, Pervaiz,Ali Larik, Fayaz,Abbas, Qamar,Hassan, Mubashir,Raza, Hussain,Fattah, Tanzeela Abdul,Seo, Sung-Yum
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p. 3707 - 3715
(2018/06/19)
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- 1-substituted benzoyl-4-fatty acyl semicarbazide derivative, preparation method and application thereof as antibacterial agent
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The invention belongs to the technical field of antibacterial agents, and relates to a 1-substituted benzoyl-4-fatty acyl semicarbazide derivative, a preparation method and application thereof as an antibacterial agent. The compound is shown in a formula
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Paragraph 0108; 0109; 0112; 0118; 0124; 0130; 0136; 0142
(2018/09/14)
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- SELECTIVE HDAC6 INHIBITORS
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The present invention relates to novel benzohydroxamic compounds of formula (I) and (II) and pharmaceutically acceptable salts, isomers and prodrugs thereof, exhibiting a high selective inhibitory activity against histone deacetylase 6 (HDAC6) enzyme.
- -
-
Page/Page column 78; 79
(2018/11/10)
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- Synthesis, computational studies and biological evaluation of new 1-acetyl-3-aryl thiourea derivatives as potent cholinesterase inhibitors
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A new series of 1-acetyl-3-aryl thioureas (3f1–15) was synthesized by the reaction of acetyl isothiocyanate with a variety of suitably substituted aromatic anilines. The acetyl isothiocyanate was freshly prepared by reaction of corresonding acid chloride with potassium thiocyanate. The structural confirmation of all compounds was carried out by spectroscopic techniques and in case of 3a by X-ray diffraction study. The newly prepared compounds were subjected to computational studies and evaluated for their cholinesterase (acetylcholinesterase and butyrylcholinesterase) inhibition studies. Except 3f9 and 3f15, all the derivatives were found as selective inhibitor of acetylcholinesterase. Compound 3f2 (IC50 ± SEM = 1.99 ± 0.11 μM) was found to be the most potent inhibitor of acetylcholinesterase exhibited ≈11 times greater inhibitory potential than reference inhibitor i.e. neostigmine (IC50 ± SEM = 22.2 ± 3.2 μM). Compound 3f9 was found to be most potent butyrylcholinesterase inhibitor (IC50 ± SEM = 1.33 ± 0.11 μM), exhibiting ≈four times greater selectivity for butyrylcholinesterase over acetylcholinesterase. Molecular docking studies were carried out to determine the binding site interactions of these potent inhibitors with cholinesterases and also supported the experimental observations.
- Saeed, Aamer,Shakil Shah, Muhammad,Ali Larik, Fayaz,Ullah Khan, Shafi,Ali Channar, Pervaiz,Fl?rke, Ulrich,Iqbal, Jamshed
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p. 1635 - 1646
(2017/06/27)
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- Fluorescence sensing of Ag+ ions by desulfurization of an acetylthiourea derivative of 2-(2-hydroxyphenyl)benzothiazole
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A novel Ag+-selective reaction-based probe based on an acetylthiourea derivative of 2-(2-hydroxyphenyl)benzothiazole dye was investigated. The designed probe showed pronounced off-on type fluorescence signaling behavior towards Ag+ i
- Hwang, Keum Saem,Park, Ka Young,Kim, Da Bin,Chang, Suk-Kyu
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p. 413 - 419
(2017/09/02)
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- Identification of acylthiourea derivatives as potent Plk1 PBD inhibitors
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Thiourea derivatives have drawn much attention for their latent capacities of biological activities. In this study, we designed acylthiourea compounds as polo-like kinase 1 (Plk1) polo-box domain (PBD) inhibitors. A series of acylthiourea derivatives without pan assay interference structure (PAINS) were synthesized. Four compounds with halogen substituents exhibited binding affinities to Plk1 PBD in low micromole range. The most potent compound (3v) showed selectivity over other subtypes of Plk PBDs and inhibited the kinase activity of full-length Plk1.
- Yun, Taikangxiang,Qin, Tan,Liu, Ying,Lai, Luhua
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p. 229 - 236
(2016/09/09)
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- New supramolecular ferrocene incorporated N,N'-disubstituted thioureas: Synthesis, characterization, DNA binding, and antioxidant studies
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Ferrocene incorporated N,N'-disubstituted thioureas (S1-S6) were synthesized by allowing 4-ferrocenyl-3-methylaniline to react with freshly prepared aliphatic isothiocyanates and were characterized by using different analytical techniques. Based on single
- Hussain, Shabeeb,Badshah, Amin,Lal, Bhajan,Hussain, Raja Azadar,Ali, Shafqat,Tahir, Muhammad Nawaz,Altaf, Ataf Ali
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p. 2148 - 2159
(2014/08/18)
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- Discovery of N-(4-sulfamoylphenyl)thioureas as Trypanosoma brucei leucyl-tRNA synthetase inhibitors
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Human African trypanosomiasis (HAT) is one of the most neglected diseases in the tropic regions, which is fatal if not treated in time. There is an urgent need for new therapeutics, especially those in new chemical classes. Leucyl-tRNA synthetase (LeuRS) has been paid much attention as a recently clinically validated antimicrobial target. Our group has previously reported T. brucei LeuRS (TbLeuRS) inhibitors, including benzoxaboroles targeting the editing site and pyrrolinones targeting the synthetic site. Here we report the discovery of N-(4-sulfamoylphenyl)thioureas as a new class of TbLeuRS inhibitors. The R1 and R2 groups, reminiscent of the leucyl and adenyl regions of aa-AMP and aa-AMS, were optimized to result in a significant 13-fold increase of inhibitory activity (compound 19, IC 50 = 13.7 μM). Aided by ligand-protein docking, the 1,3-substitution at the central phenyl ring was predicted and proved to give significantly improved activity (59, IC50 = 1.1 μM). This work provided a new scaffold for the exploration of novel inhibitors against TbLeuRS, which may become potential therapeutics for the treatment of HAT.
- Zhang, Fenglong,Du, Jin,Wang, Qing,Hu, Qinghua,Zhang, Jiong,Ding, Dazhong,Zhao, Yaxue,Yang, Fei,Wang, Enduo,Zhou, Huchen
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p. 5310 - 5324
(2013/08/23)
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- β-Enaminonitriles in heterocyclic synthesis: Synthesis of new 1,4-dihydropyridine, tetrahydropyridine, nicotinonitrile and aminopyrazole derivatives
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A series of new pyridine, dihydropyridine, tetrahydropyridine, nicotinonitrile and pyrazole derivatives with expected biological activity were prepared through the reactions of 3-aminopent-2-enenitrile 1 with some electrophilic reagents, nucleophilic reagents, and aryl diazonium salts. The newly synthesized compounds were characterized by IR, 1H-NMR, 13C-NMR and mass spectral studies.
- Ramiz, Mahmoud M. M.,Abdel Hafiz, Ibrahim S.,Elian, Mohamed A.
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experimental part
p. 758 - 767
(2012/08/29)
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- Synthesis, characterization and antitumor activity of new ferrocene incorporated N,N′-disubstituted thioureas
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We report herein the synthesis, structural characterization and activity against human ovarian tumour models: A2780 (parent), A2780cisR (resistant to cisplatin) and A2780ZD0473R (resistant to the cisplatin analogue denoted as ZD0473)
- Lal, Bhajan,Badshah, Amin,Altaf, Ataf Ali,Tahir, Muhammad Nawaz,Ullah, Shafiq,Huq, Fazlul
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p. 14643 - 14650
(2013/01/16)
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- Activated anilide in heterocyclic synthesis: Synthesis of new dihydropyridines, dihydropyridazines and thiourea derivatives
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A series of new dihydropyridines, butanamide, dihydropyridazines and thiourea derivatives have been prepared through the reactions of 3-aminopyridine (1) and N-(pyridin-3-yl)-3-(pyridin-3-ylimino)butanamide 3 with some electrophilic reagents, aryl diazonium salts and isothiocyanates. Elementary analysis, MS, IR, and 1H NMR spectra confirmed the identity of the products. Copyright
- Hafiz, Ibrahim S.A.,Ramiz, Mahmoud M.M.,Sarhan, Ahmed A.M.
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experimental part
p. 1154 - 1162
(2012/03/26)
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- One-pot synthesis and crystal structure of N-acyl-N′-[1-(2,6- dichloro-4-trifluoromethyl)phenyl-3-cyano-1H-pyrazol-5-yl]thioureas
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Nine novel thiourea derivatives containing pyrazole rings have been prepared in good yields by the reaction of 5-amino-3-cyano-1-(2,6-dichloro-4- trifluoromethylphenyl)pyrazole with acylisothiocyanates, which were generated in situ by potassium thiocyanate and different acyl chlorides in one pot. N-Benzoyl-N′-[1-(2,6-dichloro-4-trifluoromethyl)phenyl-3-cyano-1H-pyrazol- 5-yl]thiourea was characterised by a single crystal X-ray diffraction study.
- Zhang, Xiaohong,He, Hui,Xu, Mei,Zhong, Ping
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experimental part
p. 323 - 325
(2011/10/02)
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- Synthesis of acyl thiourea derivatives of chitosan and their antimicrobial activities in vitro
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Three different acyl thiourea derivatives of chitosan (CS) were synthesized and their structures were characterized by FT-IR spectroscopy and elemental analysis. The antimicrobial behaviors of CS and its derivatives against four species of bacteria (Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Sarcina) and four crop-threatening pathogenic fungi (Alternaria solani, Fusarium oxysporum f. sp. vasinfectum, Colletotrichum gloeosporioides (Penz.) Saec, and Phyllisticta zingiberi) were investigated. The results indicated that the antimicrobial activities of the acyl thiourea derivatives are much better than that of the parent CS. The minimum value of MIC and MBC of the derivatives against E. coli was 15.62 and 62.49 μg/mL, respectively. All of the acyl thiourea derivatives had a significant inhibitory effect on the fungi in concentrations of 50-500 μg/mL; the maximum inhibitory index was 66.67%. The antifungal activities of the chloracetyl thiourea derivatives of CS are noticeably higher than the acetyl and benzoyl thiourea derivatives. The degree of grafting of the acyl thiourea group in the derivatives was related to antifungal activity; higher substitution resulted in stronger antifungal activity.
- Zhong, Zhimei,Xing, Ronge,Liu, Song,Wang, Lin,Cai, Shengbao,Li, Pengcheng
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p. 566 - 570
(2008/09/21)
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- Unexpected formation of benzothiazoles in the synthesis of new heterocycles: Benzo-1,2,4-dithiazines
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The synthesis of benzo-1,2,4-dithiazines was investigated presuming a reversible sulfur-sulfur bond formation. 2-Aminothiophenol, when allowed to react with isothiocyanates, provided benzothiazoles. 2,2′-Diaminodiphenyl disulfide underwent cyclizations very readily without any reducing agent to give, according to the reaction conditions, benzothiazoles or benzo-1,2,4-dithiazines. The developed procedure offers a simple and convenient way to prepare the title compounds in very good to excellent yields. Until now, benzo-1,2,4-dithiazines as well as 2,2′-diaminodiphenyl disulfides bearing aminocarbonothioyl groups were unknown. Georg Thieme Verlag Stuttgart.
- Fajkusova, Dagmar,Pazdera, Pavel
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p. 1297 - 1305
(2008/12/22)
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- Synthesis and structure of thia and selena heterocycles containing cycloamidine substructures
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Cyclization of a bis-arylimidoyl chloride with an acylselenourea leads to the construction of a 1,3-selenazolidine with a heteroradialene structure. Another reaction of the bis-arylimidoyl chloride (hydrazinolysis) leads to the formation of Δ2-1,2-diazetines, which we have shown previously to be reactive precursors for ring transformation reactions that yield unusual heterocycles. We now demonstrate that the reaction of these Δ2- 1,2-diazetines with various isothio- or isoselenocyanates affords an efficient entry to highly substituted 1,3,4-thia- or -selenadiazines. The structures of these novel derivatives were confirmed by NMR and mass spectroscopy, elemental analysis, and X-ray structural analysis. Detailed multidimensional 77Se NMR experiments as well as density functional theory (DFT) calculations show structural specifics of these compounds. Georg Thieme Verlag Stuttgart.
- Fleischhauer, Jan,Beckert, Rainer,Guenther, Wolfgang,Kluge, Stefan,Zahn, Stefan,Weston, Jennie,Berg, Dorothea,Goerls, Helmar
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p. 2839 - 2848
(2008/03/11)
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- Synthesis and antibacterial activity of new N-acyl-N′-(3-chloro-4- fluorophenyl)thioureas
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A new series of N-acyl-N′-(3-chloro-4-fluorophenyl)thioureas have been prepared in excellent yield by the reaction of acylthiocyanates and 3-chloro-4-fluoroaniline under solid-liquid phase transfer catalysis using PEG-400. All synthesised compounds were screened against Escherichia coli and Staphylococcus aureus in DMF for evaluating their antibacterial activity. 2d, 2e, 2f and 2g showed good activity at 50 μg/ml dilution.
- Khazi,Koti,Chadha, Monica V.,Mahajanshetti
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p. 761 - 763
(2007/10/03)
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- Method carboxy terminal protein or peptide sequencing
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The present invention provides for an efficient and novel method for the C-terminal sequencing of proteins or peptides by use of acetyl chloride or phosphoryl chloride by reaction with a suitable isothiocyanate for derivitazation of the carboxy terminus to a thiohydantoin amino acid derivative, under acidic conditions. Cleavage of the derivatized thiohydantoin amino acid may occur by use of thiocyanic acid and acetic acid in water and also by the novel means using a buffer and a potassium or sodium thiocyanate or potassium or sodium dithionite reagent. The present invention also provides for an novel and efficient means for the C-terminal sequencing of proteins or peptides by a two or three step process which comprises first reacting the peptide or protein with an acid chloride reagent, such as acetyl chloride, or phosphoryl chloride. The stable protein carboxy terminal amino acid chloride is then reacted with an organic isothiocyanate, an organic salt thiocyanate, or a metal thiocyanate to yield a thiohydantoin amino acid derivative. This thiohydantoin amino acid derivative may be cleaved using either acidic or basic condition, preferably using the novel reagents disclosed above.
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- Vibrational spectra and conformational behaviour of carbonyl isothiocyanates X-CO-NCS, X=F, Cl, Br, MeO, EtO, and acetyl isothiocyanate CH3-CO-NCS
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Vibrational data for five carbonyl isothiocyanates X-CO-NCS, with X-f, Cl, Br, MeO and EtO, and for acetyl isothiocyanate CH3-CO-NCS are reported.Detailed assignments for the infrared and Raman data of the -F, -Cl and -CH3 species are given.The vapour phase IR spectrum of acetyl isothiocyanate suggests the presence of the cisoid conformer only but the spectra of all the carbonyl isothiocyanates show features which are interpreted in terms of both cisoid and transoid conformers being present.Temperature dependent IR data show that for X=Cl and Br the transoid conformation is more stable while for X=F, Meo and EtO the cisoid form is preferred.The conformeric stabilities and vibrational data are compared with recent results for the corresponding isocyanato species.
- Campbell, Nicole L.,Gillis, Cyril J.,Klapstein, Dieter,Nau, Werner M.,Balfour, Walter J.,Fougere, Scott G.
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p. 787 - 798
(2007/10/02)
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- Radical-Based Deoxygenation of Aliphatic Alcohols via Thioxocarbamate Derivatives
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N-Phenylthioxocarbamates, obtained from the reaction of alcohols with phenyl isothiocyanate in the presence of NaH, were reduced with various silanes such as triethylsilane, triphenylsilane, and tris(trimethylsilyl)silane, as well as tributylstannane under radical conditions to give deoxygenated products of the corresponding alcohols in excellent yields.The reaction was applicable to not only simple aliphatic alcohols but also sugars and nucleosides.Regio- and stereoselective deuteration using deuteriosilanes and deuteriostannane was also examined under the similar conditions.
- Oba, Makoto,Nishiyama, Kozaburo
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p. 10193 - 10200
(2007/10/02)
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- STUDIES WITH POLYFUNCTIONALLY SUBSTITUTED HETEROAROMATICS: SYNTHESIS OF SEVERAL NEW THIAZOLE, PYRAZOLOTRIAZINES AND OF POLYFUNCTIONALLY SUBSTITUTED PYRIDINES AND PYRIMIDINES.
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Several thiazolin-4-one (3), 1,2,4-triazinethione (13), pyrazolo-1,2,4-triazine (16) and pyridine (23) derivatives could be obtained via the reaction of iminoether (1) derivative with thioglycolic acid, aryldiazonium chloride, 3-arylpyrazol-5-yl di
- Elghandour, Ahmed H. H.,Ibrahim, Mohamed K. A.,Elshikh, Said M. M.,Ali, Fawzy M. M.
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p. 9295 - 9304
(2007/10/02)
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- Reaction of Hydrazidoyl Halides with Thiocyanate Anion: Synthesis of Thiadiazolines and Thiadiazoloquinazoline
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Hydrazidoyl chlorides (1a-d) react with potassium thiocyanate to give 5-imino-Δ2-1,3,4-thiadiazoline derivatives (4a-d).The corresponding N-acetyl-, N-benzoyl- and N-ethoxycarbonyl-thiadiazolines (5, 6 and 7) have been obtained via 1,3-dipolar cycloaddition of 1d to acetyl isothiocyanate, benzoyl isothiocyanate and ethoxycarbonyl isothiocyanate or via acylation reaction of compound 4d with acetyl chloride, benzoyl chloride and ethyl chloroformate.Compound 1e, however, on reaction with potassium thiocyanate furnishes directly the thiadiazoloquinazoline (8).Condensation of 4a with α-halogenketones and isothiocyanates gives N-alkylderivatives (9-11) and thioureas (12-14) respectively.Compound 4c on treatment with nitrous acid followed by reduction gives hydrazine derivative (16) via the intermediate 15.Bromination of 4b furnishes 17 which on reaction with cyanide ion furnishes the corresponding cyanoacetyl derivative (18).
- Ibrahim, Mohamed Kamal Ahmed
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p. 120 - 122
(2007/10/02)
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- Synthesis and fungicidal activities of some 2-aryloxymethyl-1,3,4-thiadiazolo-quinazolin-4-ones and 2-aryloxymethyl-5-substituted-1,3,4-thiadiazolo-1,3,5-triazine-7-thiones
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Several 2-aryloxymethyl-1,3,4-thiadiazolo-quinazolin-4-ones (Va-e) and 2-aryloxymethyl-5-substituted-1,3,4-thiadiazolo-1,3,5-triazine-7-thiones (IIIa-e) have been synthesized and screened for their antifungal activity against Aspergillus niger and Helminthosporium oryzae.
- Tiwari, Nirupama,Chaturvedi, Bandana,Nizamuddin
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p. 200 - 202
(2007/10/02)
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- 1,3-Oxazines and Related Compounds. IX. Alkylation, Acylation, and Cleavage Reaction of 6-Methyl-4-oxo-2-thioxo-3,4-dihydro-2H-1,3-oxazine
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Alkylation of the title compound (2) with alkyl halides in the presence of Et3N proceeded exclusively on the sulfur atom to give the alkyl-1,3-oxazine derivatives.Acylation with acyl chlorides took place regioselectively on the nitrogen atom, giving the N-acyl derivatives. 1,3-Oxazine 2 was found to undergo cleavage of the ring into acetylketene and thiocyanic acid.Hence, treatment of 2 with alkyl halides in the presence of K2CO3 gave alkyl thiocyanates; treatment with active methylene compounds afforded γ-pyrone derivatives.N-Acyl derivatives of 2 also underwent thermal cleavage of the ring, leading to the corresponding acyl isothiocyanates.Keywords - 2-thioxo-4-oxo-1,3-oxazine; acetylketene; thiocyanic acid; acyl isothiocyanate; alkyl thiocyanate; acylation; alkylation; substituted γ-pyrone.
- Yamamoto, Yutaka,Morita, Yasuo
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p. 2957 - 2962
(2007/10/02)
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- Reactions of (E)-1-Methoxy-1-trimethylsiloxyprop-1-ene with Acyl Isocyanates and Acyl Isothiocyanates
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Reaction of aryl acyl,and alkyl acyl isocyanates with (E)-1-methoxy-1-trimethylsiloxyprop-1-ene affords high yields of various methyl 3-acylamino-2-methyl-3-oxopropanoates.The corresponding acyl isothiocyanates give a variety of products depending on the structure of the isothiocyanate.
- Cambie, Richard C.,Davis, Paul F.,Rutledge, Peter S.,Woodgate, Paul D.
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p. 2073 - 2084
(2007/10/02)
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- SYNTHESIS OF ISOTHIOCYANATOPHOSPHORANES AND ISOTHIOCYANATOPHOSPHONIUM SALTS VIA OXIDATIVE ADDITION OF THIOCYANOGEN AND LIGAND SUBSTITUTION. NOVEL REAGENTS FOR CONVERTING HYDROXY GROUPS INTO THIOCYANATE AND ISOTHIOCYANATE FUNCTIONS UNDER MILD CONDITIONS
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The oxidative addition of thiocyanogen to triphenilphosphine has been investigated by (31)P NMR spectroscopy showing the formation of the isothiocyanatophosphonium salt 8.The analogous reaction between thiocyanogen and alkyl o-phenylene phosphites 7 leads to diisothiocyanatophosphoranes 9.The same products were prepared via ligand substitution from the corresponding chlorophosphonium salt 12 and alkyldichloro-o-phenylene phosphoranes 13 by the action of potassium thiocyanate in the presence of 18-crown-6-ether or more conveniently using lead thiocyanate.The phosphonium salt 8 and phosphoranes 9 were employed as convenient novel reagents for converting hydroxy groups into thiocyanate and isothiocyanate function with high stereoselectivity under very mild conditions.The efficient synthesis of acylisothiocyanates RCONCS,R2P(O)NCS and R2P(S)NCS via addition of thiocyanogen to mixed anhydrides is of special interest.
- Burski, J.,Kieszkowski, J.,Michalski, J.,Pakulski, M.,Skowronska, A.
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p. 4175 - 4182
(2007/10/02)
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- Phosphonothioureide anthelmintics
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Aryl- and heterocyclic substituted phosphonothioureide compounds useful as anthelmintics.
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- Phosphonoureide and phosphonothioureide anthelmintics
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This invention relates to novel anthelmintic compounds containing an arylene or divalent heterocyclic ring whose free valences are satisfied by 1. a disubstituted phosphoryl ureido or thioureido group and 2. an amino group or a substituted amido or thioamido group, To compositions containing them, and to methods of using them for the treatment of intestinal parasites in mammals and birds.
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