Synthesis and Antimicrobial Activities of Novel Series of 1-((4-Methyl-2-Substituted Thiazol-5-yl)Methyleneam INO)-2-Substituted Isothiourea Derivatives

Shelke, Shivaji H.; Mhaske, Pravin C.; Hande, Pankaj E.; Bobade, Vivek D.

doi:10.1080/10426507.2012.745542

Cited by 14 publications

(9 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Several substituted isothiourea derivatives were reported to possess significant cardiovascular properties as nitric oxide synthase inhibitors [1][2][3][4][5], and calcium channel blockers [6]. Isothiourea derivatives were also reported to display potent antimicrobial [7,8], anticancer [9,10], and anti-anthelmintic [11] activities. The incorporation of the highly lipophilic adamantyl group positively modulates the therapeutic index of several compounds through various mechanisms [12,13].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C₂₄H₂₇ClN₂S

El-Emam

Al-Omary

Al-Rasheed

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

C 24 H 27 ClN 2 S, triclinic P1 (no. 2), a = 7.1670(3) Å, b = 12.2734(6) Å, c = 13.1560(6) Å, α = 109.605(2)°, β = 96.515(2)°, γ = 97.312(2)°, V = 1066.08(8) Å 3 , Z = 2, The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialBenzyl bromide (342 mg, 2.0 mmol) and anhydrous potassium carbonate (277 mg, 2.0 mmol) were added to a solution 1-(adamantan-1-yl)-3-(3-chlorophenyl)thiourea (642 mg, 2.0 mmol), in acetone (10 mL), and the mixture was heated under reflux for 3 h. The solvent was distilled off in vacuo, and the residue was washed with water, dried and recrystallized from ethanol to yield 625 mg (76%) of the title compound as transparent block crystals. M.P.: 367-369 K. Single crystals were obtained by slow evaporation of a EtOH/CHCl 3 (1:1) solution at room temperature.

show abstract

Section: Discussionmentioning

confidence: 99%

Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C₂₄H₂₇ClN₂S

El-Emam

Al-Omary

Al-Rasheed

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

show abstract

“…9, 10 In this study, whole-cell screening assays of libraries of substituted thiazoles and thiadiazoles identified a novel lead compound that displayed notable antibacterial activity against MRSA. The lead compound 1a (Figure 1) consists of a thiazole central ring connected to two unique structural features – a cationic element at the C5-position and a lipophilic moiety at the C2-position.…”

Section: Introductionmentioning

confidence: 97%

Discovery and Characterization of Potent Thiazoles versus Methicillin- and Vancomycin-Resistant Staphylococcus aureus

et al. 2014

View full text Add to dashboard Cite

Methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA & VRSA) infections are growing global health concerns. Structure-activity-relationships of phenylthiazoles as a new antimicrobial class have been addressed. We present 10 thiazole derivatives that exhibit strong activity against 18 clinical strains of MRSA and VRSA with acceptable PK profile. Three derivatives revealed an advantage over vancomycin by rapidly eliminating MRSA growth within six hours and no derivatives are toxic to HeLa cells at a concentration of 11 μg/mL.

show abstract

“…The syntheses of compounds 1a – d to 7a – d are reported in our previous papers. Ethyl 2‐arylthiazole‐4‐carboxylate, 1a – d on reduction of carboethoxy group followed by selective oxidation using iodoxy benzoic acid furnished 2‐arylthiazole‐4‐carbaldehyde 2a – d . Aldehyde 2a – d on reaction with iodine and ammonia in tetrahydrofuran gave 2‐arylthiazole‐4‐carbonitrile 3a – d .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, and Antimicrobial Screening of 4″‐methyl‐2,2″‐diaryl‐4,2′:4′,5″‐terthiazole Derivatives

Nalawade

Mhaske

Shinde

et al. 2018

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

A series of novel 4″‐methyl‐2,2″‐diaryl‐4,2′:4′,5″‐terthiazole (8a‐p) derivatives has been synthesized and screened for antibacterial activity against four pathogenic bacteria, Escherichia coli, Pseudomonas flurescence, Staphylococcus aureus, and Bacillus subtilis. Among them, compounds 8a and 8j exhibited excellent antibacterial activity with minimum inhibitory concentration range of 1.0 to 5.3 μg/mL and compounds 8m and 8p exhibited moderate to good antibacterial activity with minimum inhibitory concentration range of 16.9 to 29.7 μg/mL against all tested strains. All the synthesized compounds were screened for their in vitro antifungal activity against Cocinida candida. Most of the compounds reported moderate antifungal activity. This study provides valuable directions to our ongoing endeavor of rationally designing more potent antimicrobial agent.

show abstract

Synthesis and Antimicrobial Activities of Novel Series of 1-((4-Methyl-2-Substituted Thiazol-5-yl)Methyleneam INO)-2-Substituted Isothiourea Derivatives

Cited by 14 publications

References 28 publications

Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C₂₄H₂₇ClN₂S

Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C₂₄H₂₇ClN₂S

Discovery and Characterization of Potent Thiazoles versus Methicillin- and Vancomycin-Resistant Staphylococcus aureus

Synthesis, Characterization, and Antimicrobial Screening of 4″‐methyl‐2,2″‐diaryl‐4,2′:4′,5″‐terthiazole Derivatives

Contact Info

Product

Resources

About

Synthesis and Antimicrobial Activities of Novel Series of 1-((4-Methyl-2-Substituted Thiazol-5-yl)Methyleneam INO)-2-Substituted Isothiourea Derivatives

Cited by 14 publications

References 28 publications

Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C24H27ClN2S

Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C24H27ClN2S

Discovery and Characterization of Potent Thiazoles versus Methicillin- and Vancomycin-Resistant Staphylococcus aureus

Synthesis, Characterization, and Antimicrobial Screening of 4″‐methyl‐2,2″‐diaryl‐4,2′:4′,5″‐terthiazole Derivatives

Contact Info

Product

Resources

About

Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C₂₄H₂₇ClN₂S

Crystal structure of (Z)-3-(adamantan-1-yl)-1-(3-chlorophenyl)-S-benzylisothiourea, C₂₄H₂₇ClN₂S