Synthesis of N-substituted acetamide derivatives of azinane-bearing 1,3,4-oxadiazole nucleus and screening for antibacterial activity

Iqbal, Kashif; Jamal, Qaiser; Iqbal, Javeid; Afreen, Maria Sadaf; Sandhu, Muhammad Zeeshan Ahmed; Dar, Eshwa; Farooq, Umar; Mushtaq, Mohammad Fahd; Arshad, Numera; Iqbal, Majid

doi:10.4314/tjpr.v16i2.23

Cited by 12 publications

(11 citation statements)

References 12 publications

(12 reference statements)

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“…[2} The encoding proto‐oncogene serves as an important tumor marker, as mutations resulting in aberrant c‐Kit signaling have been implicated in the development, migration, and recurrence of various cancers, most notably acute myelogenous leukemia and gastrointestinal stromal tumors . The clinical relevance of this causal nexus is underlined by the success of kinase inhibitors such as Imatinib (Gleevec), an approved drug for the treatment of exactly these tumors, which hits c‐Kit as one of its molecular targets …”

Section: Methodsmentioning

confidence: 99%

Concise Total Synthesis of Enigmazole A

et al. 2015

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An efficient entry into the phosphorylated marine macrolide enigmazole A is described. Enigmazole A interferes with c-Kit signaling by an as yet unknown mode of action and is therefore a potential lead in the quest for novel anticancer agents. Key to success is a gold-catalyzed cascade comprising a [3,3]-sigmatropic rearrangement of a propargyl acetate along the periphery of a macrocyclic scaffold, followed by a transannular hydroalkoxylation of the resulting transient allenyl acetate. This transformation mandated the use of a chiral gold catalyst to ensure a matching double-asymmetric setting. Other noteworthy steps are the preparation of the oxazole building block by a palladium-catalyzed C-H activation, as well as the smooth ring-closing alkyne metathesis of a diyne substrate bearing a propargylic leaving group, which has only little precedent.

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Section: Methodsmentioning

confidence: 99%

Concise Total Synthesis of Enigmazole A

et al. 2015

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“…The progress and completion of reactions was checked by TLC on pre-coated silica gel plates by UV 254 lamp along with ethyl acetate and nhexane (different polarity solvent system). Griffin and George apparatus was employed to calculate the melting points of compounds 6a-l [16]. The presence of various functional groups in compounds 6a-l were identified by IR technique using Jasco-320-A spectrophotometer.…”

Section: Experimental Generalmentioning

confidence: 99%

“…The current work is the continuity of our efforts to add some new compounds in the field of synthetic chemistry having various modifications in the structural frame work. In the same year we have reported acetamides derivatives based on azinane bearing 1,3,4-oxadiazole as active anti-bacterial agents [16]. The current study was to evaluate the effect of propanamide bearing three carbons in place of acetamides bearing two carbons.…”

Section: Introductionmentioning

confidence: 98%

Synthesis of some new propanamide derivatives bearing 4- piperidinyl-1,3,4-oxadiazole, and their evaluation as promising anticancer agents

Rehman¹,

Ahtzaz²,

Abbasi³

et al. 2018

Trop. J. Pharm Res

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Purpose: To sequentially synthesize piperidine-4-carboxylic acid ethyl ester-appended 1,3,4-oxadiazole hybrids and to evaluate them as anticancer agents. Methods: Ethyl 1-[(4-methylphenyl)sulfonyl]-4-piperidinecarboxylate (1) was synthesized from 4methylbenzenesulfonylchloride (a) and ethyl 4-piperidinecarboxylate (b). Compound (1) was converted into ethyl 1-[(4-methylphenyl)sulfonyl]-4-piperidine carbohydrazides (2) and 5-{1-[(4methylphenyl)sulfonyl]-4-piperidinyl}-1,3,4-oxadiazole-2-thiol (3) respectively. A variety of aryl amine (4a-l) were treated with 2-bromopropionylbromide to synthesize an array of propanamide (5a-l). Finally, 5-{1-[(4-methylphenyl)sulfonyl]-4-piperidinyl}-1,3,4-oxadiazole-2-thiol (3) and propanamides (5a-l) were reacted to synthesize target compounds (6a-l). Purity compounds 6a-l was confirmed by spectroscopic techniques like (1 H-NMR), (13 C-NMR) and EI-MS. To determine their anticancer potential, the change in absorbance of mixture and cell line before and after incubation was determined. Results: All the compounds 6a-l were successfully synthesized in 73-85 % yield. Compounds 6h, 6j and 6e have low IC50 (±SD) values of 20.12 ± 6.20, 10.84 ± 4.2 and 24.57 ± 1.62 µM to act as strong anticancer agents relative to doxorubicin (0.92 ± 0.1 µM) used as a reference. Conclusion: The synthesized propanamide derivatives bearing 4-piperidinyl-1,3,4-oxadiazole are potential anticancer agents, but further studies, especially in vivo, are required to ascertain their therapeutic usefulness.

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“…The kinase inhibitor imatinib, which was introduced into the market in 2001, paved the way for the development of protein kinase inhibitors. Today, such inhibitors are approved for the treatment of cancer, inflammation and rheumatoid arthritis …”

Section: Introductionmentioning

confidence: 99%

Synthesis and SAR of Tetracyclic Inhibitors of Protein Kinase CK2 Derived from Furocarbazole W16

et al. 2020

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The serine/threonine kinase CK2 modulates the activity of more than 300 proteins and thus plays a crucial role in various physiological and pathophysiological processes including neurodegenerative disorders of the central nervous system and cancer. The enzymatic activity of CK2 is controlled by the equilibrium between the heterotetrameric holoenzyme CK2α 2 β 2 and its monomeric subunits CK2α and CK2β. A series of) was prepared in an one-pot, three-component Levy reaction. The stereochemistry of the tetracyclic compounds was analyzed. Additionally, the chemically labile anhydride structure of the furocarbazoles 3 was replaced by a more stable imide (9) and N-methylimide (10) substructure. The enantiomer (À )-3 a (K i = 4.9 μM) of the lead compound (+)-3 a (K i = 31 μM) showed a more than sixfold increased inhibition of the CK2α/CK2β interaction (protein-protein interaction inhibition, PPII) in a microscale thermophoresis (MST) assay. However, (À )-3 a did not show an increased enzyme inhibition of the CK2α 2 β 2 holoenzyme, the CK2α subunit or the mutated CK2α' C336S subunit in the capillary electrophoresis assay. In the pyrrolocarbazole series, the imide (À )-9 a (K i = 3.6 μM) and the N-methylimide (+)-10 a (K i = 2.8 μM) represent the most promising inhibitors of the CK2α/CK2β interaction. However, neither compound could inhibit enzymatic activity. Unexpectedly, the racemic tetracyclic pyrrolocarbazole (�)-12, with a carboxy moiety in the 4-position, displays the highest CK2α/CK2β interaction inhibition (K i = 1.8 μM) of this series of compounds.

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Synthesis of N-substituted acetamide derivatives of azinane-bearing 1,3,4-oxadiazole nucleus and screening for antibacterial activity

Cited by 12 publications

References 12 publications

Concise Total Synthesis of Enigmazole A

Concise Total Synthesis of Enigmazole A

Synthesis of some new propanamide derivatives bearing 4- piperidinyl-1,3,4-oxadiazole, and their evaluation as promising anticancer agents

Synthesis and SAR of Tetracyclic Inhibitors of Protein Kinase CK2 Derived from Furocarbazole W16

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