Synthesis and biological evaluation of triazepane derivatives as DPP-IV inhibitors

Park, Woul Seong; Jun, Mi Ae; Shin, Mi Sik; Kwon, Sung Wook; Kang, Seung Kyu; Kim, Ki Young; Rhee, Sang Dal; Bae, Myung Ae; Narsaiah, B.; Lee, Duck‐Hyung; Cheon, Hyae Gyeong; Ahn, Jin Hee; Kim, Sung Soo

doi:10.1016/j.jfluchem.2009.08.001

Cited by 13 publications

(4 citation statements)

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“…[ 35,36 ] Triazepine derivatives have the ability to inhibit the dipeptidyl peptidase IV (DPP‐IV) and treatment of diabetes. [ 37 ] In addition, 1,2,4‐triazepines have many biological activities like renal vasodilator, salidiuretic, analgesic, antioxidant, and immunomodulating activities. [ 35,38 ] The fusion of triazepine to the pyrimidine moiety increases the improvement of the biological activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new pyrazoles, oxadiazoles, triazoles, pyrrolotriazines, and pyrrolotriazepines as potential cytotoxic agents

Abu‐Hashem

2021

Journal of Heterocyclic Chem

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4‐Oxo‐4‐phenylbutanehydrazide (1) reacted with many active methylene reagents such as acetylacetone, diethylmalonate, ethylacetoacetate, ethylcyanoacetate, benzoyl‐acetonitrile, and malononitrile under neat conditions to afford the corresponding pyrazoles (2–7), also, treatment of butanehydrazide (1) with electrophilic reagents as triethylorthoformate, dimethylformamide‐dimethylacetal, acetic anhydride, and carbon disulfide to give 1,3,4‐oxadiazoles (8,10,11) and N′‐acetyl‐butanehydrazide (9). Reacted of butanehydrazide (1) with potassium thiocyanate gave 1,2,4‐triazoles (12). Similarly, treatment of (1) with chloroacetamide gave 1,2,4‐triazinones (13). The pyrrolotriazinones (14) was obtained by cyclization of (13). Also, butanehydrazide (1) was utilized as a starting material for the synthesized of new Schiff bases as N′‐(4‐sub‐benzylidene)‐phenylbutane‐hydrazide (15a‐c), which are used as an initiative to prepare new compounds such as 1,2,4‐triazepinones (16a‐c), pyrrolotriazepinones (17a‐c), 1,2,4‐triazines (18a‐c), and pyrrolotriazines (19a‐c) by reacted of (15a‐c) with each chloroacetamide or formamide. The chemical structure of the newly prepared compounds was determined through the spectrum data, including IR, NMR, and MS. The prepared compounds were tested for their in vitro antitumor activities. The compounds 17a‐c, 16a‐c, and 19a‐c displayed activity against several types of cancer cell lines.

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Section: Introductionmentioning

confidence: 99%

Synthesis of new pyrazoles, oxadiazoles, triazoles, pyrrolotriazines, and pyrrolotriazepines as potential cytotoxic agents

Abu‐Hashem

2021

Journal of Heterocyclic Chem

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“…Compound 131 was further converted to the final compound 133 through compound 132 or directly. Most of the synthesized compounds with the acid moiety showed potent inhibitory activity of dipeptidyl peptidase‐IV (DPP‐IV) without inhibiting CYP 3A4 (Scheme ) …”

Section: Discussionmentioning

confidence: 99%

Overview on Developed Synthesis Methods of Triazepane Heterocycles

Zeydi

2017

J Chinese Chemical Soc

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Triazepanes are important seven‐membered heterocyclic compounds with nitrogen at different positions in the ring, and have many pharmaceutical activities. Compounds with the triazepane core have attracted much attention as a result of their interesting biological properties. A study of the literature shows that there are various methods for the preparation of triazepanes. In this review, we have classified the methods based on the nitrogen position in the final triazepine products into four triazepine classes, namely TAP‐1,2,3, TAP‐1,2,4, TAP‐1,2,5, and TAP‐1,3,5.

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“…Park et al prepared a series of triazepane derivatives and evaluated their DPP‐4 inhibitory action. Of all the synthesized derivatives, compound 73 ((( R )‐4‐[1‐acetyl‐2‐{3‐amino‐4‐(2,4,5‐trifluorophenyl)butanoyl‐1,2,5‐triazepan‐5‐carbonyl}benzoic acid])) was found to be highly potent DPP‐4 inhibitor with IC 50 value of 98 nM.…”

Section: Dpp‐4 Inhibitors Actionmentioning

confidence: 99%

Emergence of promising novel DPP‐4 inhibitory heterocycles as anti‐diabetic agents: A review

Rohilla¹,

Gupta²,

Pathak³

et al. 2018

Archiv der Pharmazie

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Diabetes has turned out to be an epidemic in the recent years all over the world, and today it has become a burden on the healthcare system. Over the years, with technological advancements, different classes of antidiabetic medications have emerged, like sulfonylureas, biguanides, alpha-glucosidase inhibitors, and thiazolidinediones, but these are often loaded with serious aftermaths like hypoglycemia, weight gain, cardiovascular and renal issues. Dipeptidyl peptidase-4 (DPP-4) inhibition is an exciting and new approach in the treatment of type-2 diabetes. DPP-4 inhibitors or "gliptins" are weight neutral, pose lesser risk of hypoglycemia, and provide a long-term post-meal glycemic control. In this review, an attempt has been made to investigate novel potential compounds that can be added to the existing list of anti-diabetic drugs.

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Synthesis and biological evaluation of triazepane derivatives as DPP-IV inhibitors

Cited by 13 publications

References 29 publications

Synthesis of new pyrazoles, oxadiazoles, triazoles, pyrrolotriazines, and pyrrolotriazepines as potential cytotoxic agents

Synthesis of new pyrazoles, oxadiazoles, triazoles, pyrrolotriazines, and pyrrolotriazepines as potential cytotoxic agents

Overview on Developed Synthesis Methods of Triazepane Heterocycles

Emergence of promising novel DPP‐4 inhibitory heterocycles as anti‐diabetic agents: A review

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