Successful computer guided planned synthesis of (4R)-thiazolidine carboxylic acid and its 2-substituted analogues as urease inhibitors

Khan, Khalid Mohammed; Ullah, Zia; Lodhi, Muhammad Arif; Ali, Muhammad; Choudhary, M. Iqbal; Rahman, Atta Ur; Ul-Haq, Zaheer

doi:10.1007/s11030-005-9000-6

Cited by 23 publications

(12 citation statements)

References 10 publications

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“…4-Carboxy-4-thiazolidinyl, 2BP, and DCA were ordered from SigmaAldrich. BHTC can be easily synthesized following a protocol described previously (Khan et al, 2006;Song et al, 2009). A preparation of BHTC we synthesized using this protocol (s-BHTC) produced an NMR spectrum identical to that obtained with BHTC purchased from Sigma TimTec (p-BHTC; data not shown), and the efficacy of s-BHTC and p-BHTC in reducing Hpa spore development in Arabidopsis was nearly identical (data not shown).…”

Section: Synthetic Elicitorsmentioning

confidence: 87%

The Synthetic Elicitor 2-(5-Bromo-2-Hydroxy-Phenyl)-Thiazolidine-4-Carboxylic Acid Links Plant Immunity to Hormesis

et al. 2015

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Section: Synthetic Elicitorsmentioning

confidence: 87%

The Synthetic Elicitor 2-(5-Bromo-2-Hydroxy-Phenyl)-Thiazolidine-4-Carboxylic Acid Links Plant Immunity to Hormesis

et al. 2015

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“…Helicobacter pylori is lethal for human health as it causes the numerous stomach related disorders such as pyelonephritis, hepatic coma, peptic ulcer, and formation of kidney stones. Moreover, urease enzyme is also responsible for the decline in crop production because it deprives of the soil from an essential fertilizer urea by releasing harmful gases which may lead to global warming …”

Section: Introductionmentioning

confidence: 99%

Hybrid Pharmacophoric Approach in the Design and Synthesis of Coumarin Linked Pyrazolinyl as Urease Inhibitors, Kinetic Mechanism and Molecular Docking

Saeed

Mahesar

Channar

et al. 2017

Chemistry & Biodiversity

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The current research article reports the synthesis of coumarinyl pyrazolinyl thioamide derivatives and their biological activity as inhibitors of jack bean urease. The coumarinyl pyrazolinyl thioamides were synthesized by reacting thiosemicarbazide with newly synthesized chalcones to afford the products in good yields and the synthesized compounds were purified by recrystallization. Coumarinyl pyrazolinyl thioamide derivatives 5a - 5q showed significant activity against Urease enzyme and also exhibited good antioxidant potential. The compound 3-(2-oxo-2H-chromen-3-yl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide (5n) was found to be superior agent in the series with an IC = 0.358 ± 0.017 μm compared to standard thiourea with an IC = 4720 ± 174 μm. To undermine the binding mode of inhibition kinetic studies were performed for most potent derivative and it was found that compound 5n inhibits urease enzyme by non-competitive mode of inhibition. Molecular docking studies were carried out to delineate the binding affinity of the synthesized derivatives.

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“…21,22 TCAs (1a-c) were obtained in high yields. 18 and antineoplastic. 23,24 Similarly, it is also known that dihydroxybenzene groups are biologically active and found in the structure of many drugs and natural products.…”

Section: Resultsmentioning

confidence: 99%

Üç Thiazolidine-4-Karboksilik Asit Türevinin Pseudomonas, Acinetobacter, Staphylococcus Aureus ve Escherichia Coli Bakterilerine Karşı Antibakteriyel Özelliklerinin İncelenmesi

Genc¹,

Zengin²,

Öğütlü³

et al. 2017

Online Türk Sağlık Bilimleri Dergisi

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Çok ilaca dirençli bakterilerin tedavisi, halk sağlığı için artan bir küresel sorundur. Bu dirence ayak uydurabilmek için yeni ilaç aktif maddelerine ihtiyaç duyulmaktadır. Tiazolidin-4-karboksilik asitlerin (TCA) doğal olarak oluşan amino asitlerin çeşitli esas işlevlerini taklit ederek bakteri gelişimini engelleyebildiği bilinmektedir. Bu nedenle, ikisi yeni olan üç TCA türevinin sentezlenmesi amaçlanmış ve antibakteriyel aktiviteleri çok ilaca dirençli (MDR) bakteriler üzerinde araştırılmıştır. Bileşikler (la-c), L-Sistein hidroklorür ve dihidroksibenzaldehit türevlerinden sentezlendi ve çoklu ilaç dirençli bakterilere karşı in vitro aktiviteleri CLSI kriterlerine göre Kirby-Bauer yöntemi ile denendi. 1a-c, mevcut antibiyotiklere kıyasla S. aureus gibi Gram pozitif bakterilere ve Pseudomanas, Acinetobacter ve Escherichia coli gibi Gram negatif bakterilere karşı önemli antibakteriyel etki sergiledi. Burada, ılıman şartlar altında yüksek verimle kolaylıkla sentezlenebilen yeni potansiyel antibakteriyel maddeler bildirilmiştir. Ancak, bu üç bileşiğin daha ileri araştırmalarının ve in-vitro etkinlik testlerinin yapılması gerektiği açıktır.

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Successful computer guided planned synthesis of (4R)-thiazolidine carboxylic acid and its 2-substituted analogues as urease inhibitors

Cited by 23 publications

References 10 publications

The Synthetic Elicitor 2-(5-Bromo-2-Hydroxy-Phenyl)-Thiazolidine-4-Carboxylic Acid Links Plant Immunity to Hormesis

The Synthetic Elicitor 2-(5-Bromo-2-Hydroxy-Phenyl)-Thiazolidine-4-Carboxylic Acid Links Plant Immunity to Hormesis

Hybrid Pharmacophoric Approach in the Design and Synthesis of Coumarin Linked Pyrazolinyl as Urease Inhibitors, Kinetic Mechanism and Molecular Docking

Üç Thiazolidine-4-Karboksilik Asit Türevinin Pseudomonas, Acinetobacter, Staphylococcus Aureus ve Escherichia Coli Bakterilerine Karşı Antibakteriyel Özelliklerinin İncelenmesi

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