In vitro activity of S-(3,4-dichlorobenzyl)isothiourea hydrochloride and novel structurally related compounds against multidrug-resistant bacteria, including Pseudomonas aeruginosa and Burkholderia cepacia complex

Nicholson, A.; Perry, John D.; James, Arthur L.; Stanforth, Stephen P.; Carnell, Sonya; Wilkinson, Katy; Khan, C. M. Anjam; Soyza, Anthony De; Gould, F.K.

doi:10.1016/j.ijantimicag.2011.08.015

Cited by 22 publications

(19 citation statements)

References 23 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

“…5,6) Several groups found some derivatives with similar antibacterial activity against some bacteria through the investigation of structure-activity relationship of A22 derivatives. 7,8) However, all these derivatives thus far were modified on benzyl ring, not isothiourea.…”

mentioning

confidence: 99%

Anti-<i>Pseudomonas aeruginosa</i> Compound, 1,2,3,4-Tetrahydro-1,3,5-triazine Derivative, Exerts Its Action by Primarily Targeting MreB

Yamachika

Sugihara

Tsuji

et al. 2012

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

In order to find new anti-Pseudomonas agents, we carried out whole-cell based P. aeruginosa growth assay, and identified 1,2,3,4-tetrahydro-1,3,5-triazine (Compound A). This compound showed anti-Pseudomonas activity against wild as well as pumpless strain equally at a same concentration. Also, this compound was structurally very similar to A22, which is known to inhibit the bacterial actin-like protein MreB. By the analysis of resistant strains, the primary target of this compound in P. aeruginosa was definitely confirmed to be MreB. In addition, these compounds showed a bacteriostatic effect, and induced the morphology changes in P. aeruginosa from rod shape to sphere shape, which leads to be clinically favorable in terms of susceptibility to phagocytosis and release of endotoxin. These results display that Compound A is a very attractive compound which shows anti-P. aeruginosa activity based on inhibition of MreB without being affected by efflux pumps, and could provide a new step toward development of new promising anti-Pseudomonas agents, MreB inhibitors.

show abstract

“…In contrast, custom-made sulphur nanoparticles failed to impart any antibacterial effect at the equivalent concentrations of chemically synthesized sulphur nanoparticles [29]. In another 2012 study, Nicholson et al [30] claimed significant antimicrobial activity of two test compounds against NDM-1-producing pathogens. These compounds were isothiourea derivatives, namely "S-(3,4-dichlorobenzyl)isothiourea hydrochloride" and "S-(4-chlorobenzyl) isothiourea hydrochloride" [30].…”

Section: Some Of the Recent Attempts To Target Ndm-1-producing Bacteriamentioning

confidence: 99%

“…In another 2012 study, Nicholson et al [30] claimed significant antimicrobial activity of two test compounds against NDM-1-producing pathogens. These compounds were isothiourea derivatives, namely "S-(3,4-dichlorobenzyl)isothiourea hydrochloride" and "S-(4-chlorobenzyl) isothiourea hydrochloride" [30]. Some groups are working to find possible NDM-1-inhibition activity in quercitin, a green tea flavonoid, as well.…”

Section: Some Of the Recent Attempts To Target Ndm-1-producing Bacteriamentioning

confidence: 99%

A Region-specific Treatment Strategy To Address The Problem Of Drug Resistance By NDM-1-producing Pathogens

Ahmad¹,

Ashraf²

2013

Enz Eng

View full text Add to dashboard Cite

New Delhi metallo-β-lactamase (NDM-1) is a serious threat to the existing antibiotic armory, and a potent weapon for bacteria to aid in in their 'battle'. It has the ability to inactivate all β-lactams, except aztreonam. However, most of the NDM-1-producers also produce aztreonam hydrolysing-β-lactamases, thereby making these pathogens absolutely resistant to all β-lactams. This minireview incorporates a concise update on global epidemiology (2009-2012) of NDM-1. However, the crux of the discussion is to focus on paucity of clinically useful therapeutic options, and suggest a solution to the drug resistance threat imposed by NDM-1 bacterial enzyme. The manuscript presents a 'region-specific treatment strategy' in a lucid flowchart format. The flowchart which lies at the interface of clinical microbiology and bioinformatics is expected to be useful in containing the problem of drug resistance due to NDM-1-producing bacterial pathogens.

show abstract

In vitro activity of S-(3,4-dichlorobenzyl)isothiourea hydrochloride and novel structurally related compounds against multidrug-resistant bacteria, including Pseudomonas aeruginosa and Burkholderia cepacia complex

Cited by 22 publications

References 23 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

Anti-<i>Pseudomonas aeruginosa</i> Compound, 1,2,3,4-Tetrahydro-1,3,5-triazine Derivative, Exerts Its Action by Primarily Targeting MreB

A Region-specific Treatment Strategy To Address The Problem Of Drug Resistance By NDM-1-producing Pathogens

Contact Info

Product

Resources

About

In vitro activity of S-(3,4-dichlorobenzyl)isothiourea hydrochloride and novel structurally related compounds against multidrug-resistant bacteria, including Pseudomonas aeruginosa and Burkholderia cepacia complex

Cited by 22 publications

References 23 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

Anti-<i>Pseudomonas aeruginosa</i> Compound, 1,2,3,4-Tetrahydro-1,3,5-triazine Derivative, Exerts Its Action by Primarily Targeting MreB

A Region-specific Treatment Strategy To Address The Problem Of Drug Resistance By NDM-1-producing Pathogens

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