Separation and identification of the mixture of 2‐(3,4‐dimethoxyphenyl)‐1‐<i>n</i>‐propyl or (4‐chlorobenzyl)‐5 and (6)‐1<i>H</i>‐benzimidazolecarbonitriles

Doganc, Fatima; Alp, Mehmet; Göker, Hakan

doi:10.1002/mrc.4463

Cited by 5 publications

(5 citation statements)

References 20 publications

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“…23 Compound 19 was prepared from compound 11 according to the literature. 24 The nitrile groups of these benzimidazole carbonitriles were converted to N-hydroxy benzamidine derivatives (amidoxime derivatives, 20-29) with the presence of NH 2 OH.HCI and KOtBu in DMSO. 25…”

Section: Chemistrymentioning

confidence: 99%

“…If the product was not pure, it was purified with crystallization. Compound 10, 19 11, 24 12, 26 14, 27 and 16 24 were prepared according to the given literature methods. Compound 19 was prepared from compound 11 (0.43mmol) with the reaction of 4-chlorobenzyl chloride (0.6mmol) and sodium hydride (95%) (0.8mmol) in DMF (1 mL) and isolated as described in the literature.…”

Section: General Synthesis Of Compounds 10-19mentioning

confidence: 99%

“…Compound 19 was prepared from compound 11 (0.43mmol) with the reaction of 4-chlorobenzyl chloride (0.6mmol) and sodium hydride (95%) (0.8mmol) in DMF (1 mL) and isolated as described in the literature. 24…”

Section: General Synthesis Of Compounds 10-19mentioning

confidence: 99%

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Synthesis and Structure Elucidation of New Benzimidazole Amidoxime Derivatives

Karaaslan

2020

tjps

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Daha önce yaptığımız çalışmalarda, antiparaziter, antikanser ve antimikrobiyal etkili potent aktiviteye sahip bazı amidin türevleri sentezledik. Ancak potent aktivitelerine rağmen, amidin türevlerinin, katyonik yükleri nedeniyle biyoyararlanım açısından ciddi bir sorun oluşturduğu bilinmektedir. Bu çalışmanın temel amacı, daha önce sentezlenen etkili amidin türevlerinin biyoyararlanımlarını artırmak için, ön ilaçları olarak bilinen amidoksim türevlerini hazırlamaktır. Gereç ve Yöntemler:Hedeflenen benzimidazol amidoksimler, nitril türevlerinden hareketle sentezlenmiştir. Bu benzimidazol karbonitrillerin nitril grupları, dimetil sülfoksit içerisinde NH 2 0H.HCl ve KO-t-Bu varlığında N-hidroksi benzamidin türevlerine (amidoksim türevleri, 20-29) dönüştürülmüştür. Yeni sentezlenmiş olan amidoksim türevlerinin yapıları ise 1H-NMR, 13C-NMR ve COSY, NOESY, HSQC ve HMBC gibi bazı 2D NMR teknikleri ile açıklanmıştır.Bulgular: Bu çalışmada yeni bir seri benzimidazol amidoxim türevi bileşik sentezlenmiş ve yapıları aydınlatılmıştır.Sonuç: Daha önceki çalışmalarımızda sentezlediğimiz amidin türevleri ile literatürlerde biyolojik açıdan etkili bulduğumuz amidin türevlerinin potansiyel biyoyararlanım problemlerini çözebilmek için, bu çalışmada söz konusu potent amidinlerin ön ilaç formları olan amidoksim türevlerini hazırladık. Etkili amidin türevleri ile bu çalışmada sentezlenen amidoksim türevlerinin in vivo çalışmalarının devam eden araştırmalarımız kapsamında yapılması planlanmaktadır.

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Section: Chemistrymentioning

confidence: 99%

Section: General Synthesis Of Compounds 10-19mentioning

confidence: 99%

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Synthesis and Structure Elucidation of New Benzimidazole Amidoxime Derivatives

Karaaslan

2020

tjps

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“…Compound 10-19 were obtained by condensation of 3-amino-4-(N-substituteamino)-benzonitriles with Na2S2O5 adduct of related arylaldehydes in DMF 23 . Compound 19 was prepared from compound 11 according to the literature 24 . The nitrile groups of these benzimidazole carbonitriles were converted to Nhydroxy benzamidine derivatives (amidoxime derivatives, 20-29) with the presence of NH2OH.HCI and KOtBu in DMSO 25 .…”

Section: Chemistrymentioning

confidence: 99%

“…If the product was not pure, it was purified with crystallization. Compound 10 19 , 11 24 , 12 26 , 14 27 and 16 24 were prepared according to the given literature methods. Compound 19 was prepared from compound 11 (0.43mmol) with the reaction of 4-chlorobenzyl chloride (0.6mmol) and sodium hydride (95%)(0.8mmol) in DMF (1 ml) and isolated as described in the literature 24 .…”

Section: General Synthesis Of Compounds 10-19mentioning

confidence: 99%

Synthesis And Structure Elucidation Of New Benzimidazole Amidoxime Derivatives

KARAASLAN¹

2020

tjps

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INTRODUCTION: In our previous studies we synthesized some potent antiparasitic, anticancer and antimicrobial amidine derivatives. Despite all their potent activities, it is well known that due to their cationic charge, amidine derivatives pose a serious problem in terms of bioavailability. The main purpose of this study is to prepare amidoxime derivatives of previously synthesized potent amidine derivatives as prodrugs in order to increase their bioavailabilities. METHODS: The targeted benzimidazole amidoximes were synthesized from their nitrile derivatives. The nitrile groups of these benzimidazole carbonitriles were converted to Nhydroxy benzamidine derivatives (amidoxime derivatives, 20-29) in the presence of NH2OH.HCI and KO-t-Bu in DMSO. Structures of newly synthesized amidoxime derivatives were elucidated with 1H-NMR, 13C-NMR and some 2D NMR techniques like COSY,NOESY,HSQC and HMBC. RESULTS: A new series of benzimidazole amidoximes were synthesized and their structural elucidations were done in this study. DISCUSSION AND CONCLUSION: In order to solve the potential bioavailability problem of potent amidine derivatives, we prepared the prodrugs of those potent amidine derivatives as their amidoxime derivatives. In vivo studies of both previous amidine derivatives and amidoxime prodrugs of those amidines which were synthesized in this study are planned to perform in our ongoing studies.

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Regioselective N–alkylation of 2– (3,4–dimethoxyphenyl)imidazo[4,5–b] and [4,5–c]pyridine oxide derivatives : Synthesis and structure elucidation by NMR

Göker

Özden

2019

Journal of Molecular Structure

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Separation and identification of the mixture of 2‐(3,4‐dimethoxyphenyl)‐1‐n‐propyl or (4‐chlorobenzyl)‐5 and (6)‐1H‐benzimidazolecarbonitriles

Cited by 5 publications

References 20 publications

Synthesis and Structure Elucidation of New Benzimidazole Amidoxime Derivatives

Synthesis and Structure Elucidation of New Benzimidazole Amidoxime Derivatives

Synthesis And Structure Elucidation Of New Benzimidazole Amidoxime Derivatives

Regioselective N–alkylation of 2– (3,4–dimethoxyphenyl)imidazo[4,5–b] and [4,5–c]pyridine oxide derivatives : Synthesis and structure elucidation by NMR

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