Synthesis and in vitro antiproliferative activity of new benzothiazole derivatives

Al‐Soud, Yaseen A.; Al-Sa’doni, Haitham H.; Saeed, Bahjat A.; Jaber, Ihsan H.; Beni-Khalid, Mohammad O.; Al‐Masoudi, Najim A.; Abdul-Kadir, Tahsin; Colla, Paolo La; Busonera, Bernardetta; Sanna, Tiziana; Loddo, Roberta

doi:10.3998/ark.5550190.0009.f20

Cited by 37 publications

(2 citation statements)

References 9 publications

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“…36 The benzothiazole−piperazine backbone's anticancer properties have shown that arylsulfonamides and arylthiol derivatives are cytotoxic to hepatocellular (HepG-2), prostate (DU-145), breast (MCF-7), and CD4 + human acute Tlymphoblastic leukemia (CCRF-CEM) cell lines. 37 Novel benzothiazole−piperazine compounds were tested for cytotoxicity using colon (HCT-116), breast (MCF-7), and liver cancer cell lines. 38 These studies show that many substituted benzothiazole−piperazine compounds are active against cancer cell types.…”

Section: Introductionmentioning

confidence: 99%

“…By blocking kinase proteins, these medicines caused senescent cell death . The benzothiazole–piperazine backbone’s anticancer properties have shown that arylsulfonamides and arylthiol derivatives are cytotoxic to hepatocellular (HepG-2), prostate (DU-145), breast (MCF-7), and CD4 + human acute T-lymphoblastic leukemia (CCRF-CEM) cell lines …”

Section: Introductionmentioning

confidence: 99%

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Novel 2-Aminobenzothiazole Derivatives: Docking, Synthesis, and Biological Evaluation as Anticancer Agents

Salih,

Al-Sha’er,

Basheer

2024

ACS Omega

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Sixteen novel 2-aminobenzothiazole compounds with different amines or substituted piperazine moieties were designed, synthesized, and tested using various methods. Potential interactions were assessed by docking new compounds in the adenosine triphosphate (ATP) binding domain of the PI3Kγ enzyme (PDB code: 7JWE) by nucleophilic substitution or solvent-free/neat fusion for docked compound synthesis. Final 2-aminobenzothiazole compounds were characterized by direct probe gas chromatography-mass spectrometry (GC-MS), proton ( 1 H-NMR), carbon-13 ( 13 C-NMR), and attenuated total reflectance-infrared Fourier transform infrared (ATR FT-IR). The synthesized compounds were investigated for anticancer activities on lung cancer (A549) and breast cancer (MCF-7) cell lines. The compounds' PI3Kγ inhibition was evaluated at a 100 μM concentration. 4-Nitroaniline and piperazine-4-nitroaniline combination in OMS5 and OMS14 reduced lung and breast cancer cell line growth. IC 50 values for OMS5 and OMS14, the strongest compounds, ranged from 22.13 to 61.03 μM. OMS1 and OMS2 inhibited PI3Kγ at the highest rates (47 and 48%, respectively) at a 100 μM concentration. Results show that the PI3Kγ enzyme suppression is not the main mechanism behind these OMS5 and OMS14 anticancer effects. CDK2, Akt, mTOR, and p42/44 MAPK are affected. EGF receptor suppression matters. AKT1, AKT3, CDK1/cyclin B, PDK1 direct, PIK3CA E542 K/ PIK3R1 (p110 α/p85 α), PIK3CD/PIK3R1 (p110 δ/p85 α), and PKN inhibition were measured to evaluate the possible mechanism of compound OMS14. PIK3CD/PIK3R1 (p110 δ/p85 α) is the most, with 65% inhibition, suggesting a possible mechanism of anticancer properties. Furthermore, the NCI 60-cell line inhibition demonstrates promising broad anticancer inhibition against numerous cancer cell lines of OMS5 and OMS14, which could be good lead compounds for future development.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Novel 2-Aminobenzothiazole Derivatives: Docking, Synthesis, and Biological Evaluation as Anticancer Agents

Salih,

Al-Sha’er,

Basheer

2024

ACS Omega

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Synthesis, Spectral Characterization and Antioxidant Activity of Novel Zafirlukast Sulfonyl Derivatives

Donka

Srinivasulu

Sridhar

et al. 2016

J Chinese Chemical Soc

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A new series of cyclopentyl 3-(2-methoxy-4-(piperazine-1-carbonyl)benzyl)-1-methyl-1H-indol-5-ylcarbamate sulfonyl derivatives were synthesized by the reaclion of 4-((5-(cyclopentyloxycarbonylamino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acid (ZAK drug intermediate) with Boc piperazine in the presence of EDC.HCl, HOBt, TEA in DMF followed by deboxylation by using 2N HCl or 35% HCl in acetone to get an intermediate compound. Further, this compound was treated with various substituted benzene sulfonyl chlorides in the presence of TEA in THF to afford title compounds. All the title compounds were characterized by 1 HNMR, 13 CNMR, IR and mass spectral data. The title compounds and starting material were evaluated for their antioxidant activity by using the DPPH, H 2 O 2 and NO methods. The results revealed that some of the compounds have shown significant antioxidant activity.

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Synthesis and antimicrobial activity of new pyridine derivatives-I

2010

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2-Amino substituted benzothiazoles 2a-l and 2-chloropyridine-3-carboxylic acid 3 were used to prepare 2-[N-(substitutedbenzothiazolyl)amino]pyridine-3-carboxylic acids (4a-l) in 2-ethoxy ethanol. Acid chlorides (5a-l) were condensed with 2-hydroxyethyl piperazine (6) and 2,3-dichloropiperazine (7) to prepare amide derivatives 2-[N-(substituted benzothiazolyl)amino]pyridin-3-yl (4-(2-hydroxyethyl)piperazin-1-yl)methanones (8a-l) and 2-[N-(substituted benzothiazolyl) amino]pyridin-3-yl(2,3-dichloropiperazine-1-yl)methanones (9a-l), respectively. The structures of new compounds have been established on the basis of elemental analysis and spectral (IR, 1 H NMR, and Mass spectra) studies. The in vitro antimicrobial activity was screened for all the synthesized compounds. Variable and modest activity were observed against the investigated strains of bacteria and fungi.

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Synthesis and in vitro antiproliferative activity of new benzothiazole derivatives

Cited by 37 publications

References 9 publications

Novel 2-Aminobenzothiazole Derivatives: Docking, Synthesis, and Biological Evaluation as Anticancer Agents

Novel 2-Aminobenzothiazole Derivatives: Docking, Synthesis, and Biological Evaluation as Anticancer Agents

Synthesis, Spectral Characterization and Antioxidant Activity of Novel Zafirlukast Sulfonyl Derivatives

Synthesis and antimicrobial activity of new pyridine derivatives-I

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