Synthesis and primary cytotoxicity evaluation of new 5-nitroindole-2,3-dione derivatives

Karalı, Nilgün

doi:10.1016/s0223-5234(02)01416-2

Cited by 68 publications

(40 citation statements)

References 17 publications

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“…The infrared (IR) spectra of 5a-o showed absorption bands in the 3375-3051, 1737-1684, 1620-1599 and 1193-1149 cm -1 regions attributed to NH, C=O, C=N and C=S functions, respectively. 22,56,57 The proton nuclear magnetic resonance ( 1 H NMR) spectra displayed two separate singlets at δ 7.50-11.36 and 10.84-12.75 for indole NH and thiosemicarbazone N 2 -H. The thiosemicarbazone N 4 -H appeared as a triplet at δ 8.03-10.91 in all the cases, 22,27 except 5e, 5g and 5h, wherein it resonated as a singlet at δ 8.26, 10.91 and 10.85, respectively. Similarly, the benzyl CH 2 protons were observed as a doublet at δ 4.40-5.02 in all the cases, 22,27 except 5b, 5g and 5h; in the case of 5h they appeared as a singlet at δ 3.79, whilst in 5b and 5g they resonated together with the DMSO and DMSO, CH 3 group protons, respectively.…”

Section: Chemistry Of Compounds 5a-omentioning

confidence: 99%

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Synthesis and in vitro Bio-activity Evaluation of N4-benzyl Substituted 5-Chloroisatin- 3-thiosemicarbazones as Urease and Glycation Inhibitors

Pervez¹,

Khan²,

Iqbal³

et al. 2018

ACSi

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A series of fifteen N 4 -benzyl substituted 5-chloroisatin-3-thiosemicarbazones 5a-o were synthesized and screened mainly for their antiurease and antiglycation effects. Lemna aequinocitalis growth and Artemia salina assays were carried out to determine their phytotoxicity and cytotoxicity potential. All the compounds proved to be extremely effective urease inhibitors, demonstrating enzyme inhibition much better than the reference inhibitor, thiourea (IC 50 values 1.31 ± 0.06 to 3.24 ± 0.15 vs. 22.3 ± 1.12 μM). On the other hand, eight out of fifteen compounds tested, i.e. 5b, 5c, 5h-k, 5m and 5n were found to be potent glycation inhibitors. Of these, five viz. 5c, 5h-j and 5n proved to be exceedingly efficient, displaying glycation inhibition greater than the reference inhibitor, rutin (IC 50 values 114.51 ± 1.08 to 229.94 ± 3.40 vs. 294.5 ± 1.5 μM).

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Section: Chemistry Of Compounds 5a-omentioning

confidence: 99%

“…The main fragmentation path engaged the split of endocyclic NH-CO and exocyclic NH-CS, N-N bonds. 57 The proposed fragmentation pattern of 5i is depicted in Figure S1.…”

Section: Chemistry Of Compounds 5a-omentioning

confidence: 99%

Synthesis and in vitro Bio-activity Evaluation of N4-benzyl Substituted 5-Chloroisatin- 3-thiosemicarbazones as Urease and Glycation Inhibitors

Pervez¹,

Khan²,

Iqbal³

et al. 2018

ACSi

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“…29 Primary cytotoxicity evaluation of a series of 5-nitroindole-2,3-dione-3-thiosemicarbazone derivatives has indicated that these compounds could also act as potential new anticancer agents, since they reduced the growth of different human tumor cell lines to ≤ 32%. 30 Additionally, indole and isatin oximes can be easily prepared and are widely used as precursors in fine organic synthesis, leading to many different products, such as amine-, ether-, nitrile-, and oxazole-derivatives, 31 which were also proposed as therapeutic agents for coronary and ischemic heart disease, cardiac arrhythmia and hypertension, 32 and as antidepressants. 33 …”

Section: Oxindoles and Their Biological Activitiesmentioning

confidence: 99%

Oxindoles and copper complexes with oxindole-derivatives as potential pharmacological agents

Cerchiaro

Ferreira

2006

J. Braz. Chem. Soc.

159

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Oxindóis são compostos endógenos encontrados em fluidos e tecidos de mamíferos. Particularmente, isatina (1H-indol-2,3-diona) e seus derivados vêm mostrando uma grande variedade de efeitos no meio biológico, incluindo a inibição de monoamina oxidase, atividade bactericida, fungicida, antiviral e antiproliferativa. Pesquisas mais recentes descrevem estes compostos como inibidores de quinases, uma classe de proteínas envolvidas em várias etapas do ciclo celular. Nesta revisão, complexos de cobre(II) com ligantes derivados de oxindóis são discutidos como potenciais agentes antitumorais, em comparação com outros complexos, com base na proposição de se aliar as propriedades redox e coordenativas do metal à capacidade de afetar os processos de angiogenese e apoptose já demonstrada por esse tipo de ligante.Oxindoles are endogenous compounds found in mammalian body fluids and tissues. Particularly, isatin (1H-indole-2,3-dione) and its derivatives have shown a variety of biological effects, including inhibition of monoamine oxidase, antibacterial, antifungal, antiviral and antiproliferative activities. Recent reports have described these compounds as efficient inhibitors of kinases, a class of proteins involved in many steps of the cellular cycle. Here, some copper(II) complexes with oxindole-derived ligands are discussed as potential antitumoral agents, in comparison to other complexes, based on the proposal of a synergistic effect on adding the metal coordinating and redox properties to the already demonstrated capability of these ligands to influence the angiogenesis and apoptosis processes.

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“…Investigation of the structure-activity relationships in 3-substituted 2-indolinone derivatives revealed that halogenation at the 5-position and 3-thiosemicarbazone formation were associated with increased activity against a range of human cancer cell lines, various bacteria and viruses (6)(7)(8)(9)(10). Selective activity toward multidrug resistant (MDR) cells of several thiosemicarbazone derivatives were recently tested.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and chemotherapeutic activities of 5-chloro-1H-indole-2,3-dione-3-thiosemicarbazones

Ermut

Karalı²,

Çeti̇n³

et al. 2013

mpj

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In the light of these findings, 5-chloro-1H-indole-2,3-dione 3-thiosemicarbazone derivatives were synthesized in order to obtain more potent and less toxic compounds. The structures of the ABSTRACT: A series of 5-chloro-1H-indole-2,3-dione 3-thiosemicarbazones 3a-g were synthesized to investigate the chemotherapeutic activities. The structures of 3a-g were confirmed by the spectral data (IR, 1 H NMR, 13 C NMR-APT, 13 C NMR-DEPT, HSQC, HMBC) and elemental analysis. Anticancer activities of the compounds were evaluated using cell kinetic parameters on HeLa cells derived from human cervix carcinoma. The preliminary screening results indicated that alkyl substituted compounds 3a, 3b and 3d were more effective in mitosis phase when compared to the synthesis phase. 3a-g were tested against some DNA and RNA viruses in CRFK, HeLa, HEL, MDCK and Vero cells. None of the compounds was active against any of the RNA or DNA viruses at 100 μM. All compounds were also evaluated for antimicrobial activity against selected strains. Methyl substituted 3a and allyl substituted 3c were found to be active against S. aureus and C. albicans.

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Synthesis and primary cytotoxicity evaluation of new 5-nitroindole-2,3-dione derivatives

Cited by 68 publications

References 17 publications

Synthesis and in vitro Bio-activity Evaluation of N4-benzyl Substituted 5-Chloroisatin- 3-thiosemicarbazones as Urease and Glycation Inhibitors

Synthesis and in vitro Bio-activity Evaluation of N4-benzyl Substituted 5-Chloroisatin- 3-thiosemicarbazones as Urease and Glycation Inhibitors

Oxindoles and copper complexes with oxindole-derivatives as potential pharmacological agents

Synthesis and chemotherapeutic activities of 5-chloro-1H-indole-2,3-dione-3-thiosemicarbazones

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