7133-90-6Relevant academic research and scientific papers
Internal rotation and intramolecular hydrogen bonding in thiosalicylamide: gas phase electron diffraction study supported by quantum chemical calculations
Kolesnikova, Inna N.,Rykov, Anatolii N.,Shuvalov, Maxim V.,Shishkov, Igor F.
, p. 1993 - 2001 (2019)
The molecular structure of thiosalicylamide (2-hydroxythiobenzamide) was investigated in the gas phase at 401?K by means of gas electron diffraction (GED) combined with quantum chemical (QC) calculations. Special attention was paid to the internal rotation of the thioamide group. Structural refinement was performed taking into account rovibrational corrections to the thermal-average internuclear distances calculated with harmonic and anharmonic (cubic) MP2/cc-pVTZ force constants in terms of static and dynamic models. It was shown that both models fitted the GED data equally well. The results of the GED refinement revealed that in the equilibrium structure, the thioamide group is twisted by about 30° with respect to the phenol ring plane. This is the result of an interatomic repulsion of hydrogen atom in the amide group from the closest hydrogen atom of the benzene ring, which overcomes the energy gain from the π?π conjugation of the thioamide group and the aromatic system of thiosalicylamide. Natural bond orbital (NBO) analysis and comparison of the thiosalicylamide molecular structure with those of related compounds revealed hydrogen-bonded fragment between the hydroxyl and thiocarbonyl groups. The structure of thiosalicylamide in the gas phase was found to be markedly different from that in the solid phase due to the effect of intermolecular hydrogen bonding in the crystal.
Pyochelin Biosynthetic Metabolites Bind Iron and Promote Growth in Pseudomonads Demonstrating Siderophore-like Activity
Kaplan, Anna R.,Musaev, Djamaladdin G.,Wuest, William M.
, p. 544 - 551 (2021/03/03)
Pseudomonads employ several strategies to sequester iron vital for their survival including the use of siderophores such as pyoverdine and pyochelin. Similar in structure but significantly less studied are pyochelin biosynthetic byproducts, dihydroaeruginoic acid, aeruginoic acid, aeruginaldehyde (IQS), and aeruginol, along with two other structurally related molecules, aerugine and pyonitrins A-D, which have all been isolated from numerous Pseudomonad extracts. Because of the analogous substructure of these compounds to pyochelin, we hypothesized that they may play a role in iron homeostasis or have a biological effect on other bacterial species. Herein, we discuss the physiochemical evaluation of these molecules and disclose, for the first time, their ability to bind iron and promote growth in Pseudomonads.
METHOD OF MODULATING RIBONUCLEOTIDE REDUCTASE
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Paragraph 0027; 00165; 00174, (2020/02/14)
A method of modulating ribonucleotide reductase activity in a neoplastic cell includes administering to the cell an amount of a hydrazone or hydrazine ribonucleotide reductase modulator (RRmod), the amount being effective to inhibit neoplastic cell growth.
Multicomponent synthesis of diphenyl-1,3-thiazole-barbituric acid hybrids and their fluorescence property studies
Mahata, Alok,Bhaumick, Prabhas,Panday, Anoop Kumar,Yadav, Rahul,Parvin, Tasneem,Choudhury, Lokman H.
, p. 4798 - 4811 (2020/04/03)
A series of novel diphenyl-1,3-thiazole linked barbituric acid hybrids (4) were prepared by two catalyst-free methods from readily available starting materials. The reaction of arylglyoxal, barbituric acid and aryl thioamides in the presence of 3-4 drops of water and liquid assisted grinding (LAG) provides the corresponding trisubstituted thiazoles tethered with a barbituric acid moiety within 30 minutes. Alternatively, a sequential two-step one-pot process involving aryl nitriles, ammonium sulphide, arylglyoxal and barbituric acid in water medium was developed. In this second method, in situ thioamides were prepared at room temperature from the reaction of alkyl/aryl nitriles and ammonium sulphide in aqueous medium. Arylglyoxal and barbituric acid were added to the in situ thioamides after neutralizing the reaction medium to provide trisubstituted thiazoles linked with barbituric acid derivatives. Some of our synthesized molecules showed fluorescent properties with very good quantum yields in DMSO medium. We also observed that fluorescent quantum yields of these thiazole derivatives depend on the type of electron donating/withdrawing character of R1 and R3. R2 has a very small effect on tuning the fluorescent properties. The salient features of this work are catalyst-free reactions, wide substrate scope, green reaction conditions (liquid assisted grinding and room temperature reactions in water medium) as well as the presence of more than one pharmaceutically important heterocyclic moiety with fluorescent properties.
Structure-guided design of anti-cancer ribonucleotide reductase inhibitors
Misko, Tessianna A.,Liu, Yi-Ting,Harris, Michael E.,Oleinick, Nancy L.,Pink, John,Lee, Hsueh-Yun,Dealwis, Chris G.
, p. 438 - 450 (2019/01/14)
Ribonucleotide reductase (RR) catalyses the rate-limiting step of dNTP synthesis, establishing it as an important cancer target. While RR is traditionally inhibited by nucleoside-based antimetabolites, we recently discovered a naphthyl salicyl acyl hydrazone-based inhibitor (NSAH) that binds reversibly to the catalytic site (C-site). Here we report the synthesis and in vitro evaluation of 13 distinct compounds (TP1-13) with improved binding to hRR over NSAH (TP8), with lower KD’s and more predicted residue interactions. Moreover, TP6 displayed the greatest growth inhibiting effect in the Panc1 pancreatic cancer cell line with an IC50 of 0.393 μM. This represents more than a 2-fold improvement over NSAH, making TP6 the most potent compound against pancreatic cancer emerging from the hydrazone inhibitors. NSAH was optimised by the addition of cyclic and polar groups replacing the naphthyl moiety, which occupies the phosphate-binding pocket in the C-site, establishing a new direction in inhibitor design.
Chromogenic and fluorogenic sensing of Cu2+ based on coumarin
Helal, Aasif,Or Rashid, Mohammad Harun,Choi, Cheol-Ho,Kim, Hong-Seok
body text, p. 2794 - 2802 (2011/05/02)
A new highly selective, reversible, chromogenic, and fluorogenic chemosensor (4) based on thiazole-coumarin moieties for quantification of copper ions in aqueous-DMSO was designed and synthesized. The mechanism of fluorescence was based on ICT, which was modified by the introduction of an electron-donating diethylamino group making it chromogenic and increasing the binding affinity. The selectivity toward copper ions was not affected by the presence of representative alkali metals, alkali earth metals, or other transition metals.
Thiazole-based chemosensor II: Synthesis and fluorescence sensing of fluoride ions based on inhibition of ESIPT
Helal, Aasif,Thao, Nugen Thi Thu,Lee, Soon W.,Kim, Hong-Seok
body text, p. 87 - 94 (2010/12/24)
Novel chemosensors based on 2-(2′-hydroxyphenyl)-4-phenylthiazole were synthesized and their anion sensing behaviors were investigated. Sensors 1 and 2 show fluoride ion selective behaviors related to their absorption and emission spectra amongst F-, CH3CO2-, H2PO4-, Cl-, Br-, I-, ClO4-, NO3-, and HSO4- anions. Sensor 2 shows color change upon interaction with F-. Interactions of 1, 2 and 3 with F- cause a red-shift in UV-vis absorption and a large Stokes shift in fluorescence emission due to the inhibition of ESIPT induced by the deprotonation of phenolic proton by F-. Springer Science+Business Media B.V. 2009.
7-substituted-amino-3-substituted-3-cephem-4-carboxylic acids
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, (2008/06/13)
The invention provides compounds of the formula STR1 wherein X is CH2, S or O; R1 is a 3 position substituent such as hydrogen, hydroxy, halo, trifluoromethyl, C2 F5, C1 -C6 alkyl, C1 -C6 substituted alkyl, C1 -C6 alkenyl, C1 -C6 alkynyl, CH2 O(CO)R', CH2 O(CO)NH2, CO2 R', thio(C1 -C6)alkyl, thio(C1 C6)alkenyl, oxo(C1 -C6)alkyl, phosphine oxide, quaternary ammonium group, substituted or unsubstituted thiazolothio, or oxo(C1 -C6)alkenyl; wherein R' is hydrogen, C1 -C6 alkyl, or C1 -C6 alkenyl; R2 is hydrogen or a carboxy protecting group; R3 is STR2 (CH2)n ; wherein R6 is hydrogen Me, CH2 F, CF3, C2 H5, CH2 CH2 F, CH2 CF3, C2 F5, CH2 CO2 R', CH2 CONH2, C(Me)2 CO2 R', or C(Me)2 CONH2 ; and n is 0-5; R4 is STR3 wherein Z is O, S, NH, or CH2 ; Y is CH or N; and R7 is hydrogen, C1 -C6 alkyl, CONH2, or CO2 R'; and R5 is STR4 wherein R8 is CH, N, COH, CO(C1 -C6 alkyl) CSH, or CNH2 ; and R9 is R8 as defined; said R5 optionally substituted 1-4 times with halo, OH, SH, NH2, NO2, CH3, C2 H5, CO2 R', CONH2, SO3 H, or SO2 NHR'; and salts thereof. Also, pharmaceutical formulations and methods for treating bacterial infections in man or other animals using the above compounds are disclosed.
Synthesis and in Vitro Evaluation of New Cephalosporins Exhibiting Antimicrobial Activity Against Gram-Positive Bacteria, in Particular Methicillin-Resistant Staphylococci
Lin, Ho-Shen,Rampersaud, Ashraff A.,Flokowitsch, Jane E.,Alborn, William E.,Wu, Ernie C. Y.,Preston, David A.
, p. 833 - 846 (2007/10/03)
The preparation and biological evaluation of 7β-acetamido>cephalosporins and 7β-acetamido>cephalosporins, 9a-o, substituted at the 3-position with acetyloxymethyl, chlorine, hydrogen, and methyl are described.Hantzsch's thiazole synthesis is employed to provide thiazoleacetic acids 5a-e, subsequently followed by Morpho CDI-assisted amidation to complete the synthesis of target cephalosporins 9a-o.These compounds display activity selectively against Gram-positive bacteria, but are inactive against most Gram-negative bacteria tested.Those with acetyloxymethyl at the 3-position, i.e., 9a, 9e, 9i, 9m, and 9o, exhibit activity with minimal inhibitory concentrations of 16 μg/mL or lower against four strains of methicillin-resistant staphylococci, namely Staphylococcus aureus X400 and S13E and Staphylococcus epidermidis 270 and 222.Notably, 9a displays an activity profile similar to that of vancomycin regarding its spectrum and potency.Key Words: Gram-positive bacteria; Methicillin-resistant staphylococci; Cephalosporin; Thiazole synthesis; Amidation.
Fused 7-membered cyclic compound and antipsychotic preparation containing the same
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, (2008/06/13)
A fused cyclic compound having the formula (I) or salts thereof: ψψ ψwherein both of A and B are carbonyl groups, or one represents methylene group and the other carbonyl group, Z represents a sulfur atom, or a nitrogen atom which may be substituted, or a methylene group, R represents an aromatic or heterocyclic group, which may be substituted, X represents a hydrogen atom, a halogen atom, a C1 - C5 lower alkyl group, a C1 - C5 lower alkoxy group, a C7 - C9 arylalkoxy group, a C1 - C5 lower acyloxy group, a C7 - C10 arylcarbonyloxy group, a hydroxy group, a nitro group or an ester group, and n is an integer of 2 to 10. The compounds have affinity for serotonin receptor.ψ
