81964-65-0

Upstream product

• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 108-24-7 acetic anhydride 

Downstream Products

• 1021906-74-0 C₂₀H₁₉BrN₂O₅ 
• 1021906-75-1 C₁₆H₁₉BrN₂O₅S 
• 1021906-84-2 C₂₅H₂₈BrN₃O₆ 
• 1423018-80-7 2-(2-acetamido-5-bromophenyl)-N-hexyl-2-oxoacetamide 
• 1423018-84-1 C₂₂H₃₃BrN₂O₃ 
• 1423018-87-4 C₂₈H₄₅BrN₂O₃ 
• 63243-78-7 ethyl 2-acetamido-5-bromobenzoate 
• 138825-96-4 N-(2-Carbomethoxy-4-bromo-phenyl)acetamide 
• 1385027-06-4 1-acetyl-5-bromo-3'-phenylspiro[3H-indole-3,2'-[4H]-pyrido-[3,2-e]-1,3-thiazine]-2,4'(1H)-dione 

Relevant academic research and scientific papers

Antimalarial and anti-inflammatory activities of new chloroquine and primaquine hybrids: Targeting the blockade of malaria parasite transmission

Malaria is a disease that requires new drugs not only to fight Plasmodium but also to reduce symptoms of infection such as fever and inflammation. A series of 21 hybrid compounds were designed from chloroquine (CQ) and primaquine (PQ) linked to the pharmacophoric group present in phenylacetic anti-inflammatory drugs. These compounds were designed to have dual activity: namely, to be capable of killing Plasmodium and still act on the inflammatory process caused by malaria infection. The compounds were assayed with nine different biological methods. The carbonylated CQ derivative 6 (n = 3; R1 = Cl) was more potent than CQ in vitro, and 8 (n = 4; R1 = H) reduced P. berghei parasitemia up to 37% on day 7. The carbonylated PQ derivative 17 (R = Br) was slightly less potent than PQ. The gem-difluoro PQ derivative 20 (R = Cl) exhibited high transmission blockade of the malaria sporogonic cycle in mosquitoes. Compounds 6 and 20 dose-dependently reduced nitric oxide (NO) production and inhibited TNFα production by LPS-stimulated J774A.1 macrophages. Our results indicate a viable and interesting approach in planning new chemical entities that act as transmission-blocking drugs for treating malaria caused by P. falciparum and P. vivax and the anti-inflammatory process related to this disease.

Imatinib derivatives as inhibitors of K562 cells in chronic myeloid leukemia

Imatinib was the first representative of the class of Breakpoint cluster region-Abelson murine leukemia viral oncogene homolog (BCR-ABL) tyrosine kinase inhibitors used for the treatment of chronic myeloid leukemia. Second-generation and third-generation drugs have been introduced in this therapy, affording increased patient survival. However, all BCR-ABL tyrosine kinase inhibitors have been shown to induce resistance, necessitating a search for new therapeutic options. The sunitinib, another tyrosine kinase inhibitor used in the treatment of renal cell carcinoma and gastrointestinal stromal tumors is an isatin derivative. Isatin nucleus is highly versatile for the preparation of new substances, and several tyrosine kinase inhibitors examples have been obtained using it. This work aimed to design, synthesize, and biological evaluation of new compounds using the K562 cell line, which constitutively expresses the active BCR-ABL enzyme. Three new series of imatinib derivatives have been planned from the imatinib, and all have a phenylaminopyrimidine group as the main pharmacophore. Sunitinib was used as a structural prototype to planning the series 1 (8a–e) of hybrids between sunitinib and imatinib. Series 2 and 3 are 2-oxo-2-phenyacetamide and 2,2-difluoro-2-phenylacetamide derivatives, respectively. Isatins were used as the starting materials for all series. Compounds were synthesized using simple methodologies and were obtained in high purities. The compounds were tested against K562 cells, and four showed a reduction in cell viability, with EC50 values ranging from 0.37 to 2.02 μM, some of which are close to the imatinib standard (0.21 μM).

Design, synthesis, and characterisation of glyoxylamide-based short peptides as self-assembled gels

The synthesis and supramolecular properties of novel glyoxylamide-based short peptides formed via the ring-opening reaction of N-acetylisatins in solution phase are described. The short peptides self-assembled into gels, which were examined for their mechanical and morphological characteristics using multiple spectroscopic and microscopy techniques. The critical gel concentration and mechanical strength of the self-assembled gels were influenced by the presence of electronegative substituents (such as fluoro, in 5b) or hydrophobic substituents (such as bromo, 5d) respectively in the short peptides. Moreover, in vitro cytotoxicity assays demonstrated that these compounds were non-toxic to mammalian cells.

An efficient microwave-assisted synthesis of dihydropyrazinones and bis-benzoylketones

Microwave-assisted modified Sandmeyer reactions of oximinoacetanilides, themselves obtained from substituted primary aromatic amines, in concentrated H2SO4 give isatins. N-Acetylisatins undergo ring cleavage and subsequent ring closing with alkanediamines in the presence of ethanol under MW irradiation to give the corresponding dihydropyrazinones in excellent yields. Modification of the reaction conditions affords bis-benzoylketones under MW irradiation.

Synthesis of anti-bacterial peptidomimetics derived from N-acylisatins

An efficient synthetic strategy to mono- and bis-glyoxylamide derivatives via the reaction of N-acylisatins with a range of amino acids has been developed. Using this strategy, a series of new peptidomimetics have been synthesized.

Design, synthesis, and biological evaluation of new 3-hydroxy-2-oxo-3- trifluoromethylindole as potential HIV-1 reverse transcriptase inhibitors

The trifluoromethyl group (CF3) is present in commercially available drugs of various therapeutic classes owing to its ability to modify and frequently improve their biological activities. Efavirenz is a trifluoromethylated inhibitor of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) that shows good results in anti-HIV chemotherapy. With the objective of developing efficient non-nucleoside compounds, we have designed and synthesized some new 3-hydroxy-2-oxo-3-trifluoromethylindole as potential RT inhibitors. We used different substituted isatins as starting materials. The final products contain the group CF3, present in Efavirenz, and a pharmacophoric group, oxoindole. We have used molecular docking with HIV-1 RT as a tool to design putative non-nucleoside reverse transcriptase inhibitors (NNRTIs). Based on the calculation results obtained, a series of new 3-hydroxy-2-oxo-3-trifluoromethylindoles were synthesized as a novel class of potential RT inhibitors. The results showed that these compounds are capable of important interactions with the NNRT binding site, which encouraged us to submit them for biological assay. All compounds studied are significantly active in the RNA-dependent DNA-polymerase (RDDP) assay, and were not toxic toward the Vero cell line. Hence, the designed molecules represent good starting structures for further modification and structure-activity relationship (SAR) studies. Birklaewser 2007.

Transformation of isatin 3-acylhydrazones under acetylating conditions: Synthesis and structure elucidation of 1,5′-disubstituted 3′-acetylspiro[oxindole-3,2′-[1,3,4]oxadiazolines]

Several substituted isatin 3-acylhydrazones (e.g. 1a-k, n, p, t) have been synthesized. Under acetylating conditions they were transformed into selectively acetylated derivatives (e.g., 1l, n, o, q-s) and into the novel, title spiroheterocycles (2a-i). Some side reactions occurring under various acetylating conditions are also discussed.

Isatine derivatives, their preparation and use

A method of treatment with compounds having the formula STR1 R 1 is hydrogen, C 1-6 -alkyl which may be branched, C 3-7 -cycloalkyl, benzyl, phenyl which may be substituted, acyl, hydroxy, C 1-6 -alkoxy, CH 2 CO 2 R'' wherein R'' is hydrogen or C 1-6 -alkyl which may be branched, CH 2 CN, CH 2 CONR IV R V wherein R IV and R V independently are hydrogen or C 1-6 -alkyl, or CH 2 C( NOH)NH 2 ; R 2 is hydrogen, benzyl, C 1-6 -alkyl which may be branched, or C 3-7 -cycloalkyl; R 4, R 5, R 6, R 7 independently are hydrogen, C 1-6 -alkyl which may be branched, phenyl, halogen, C 1-6 -alkoxy, NO 2, CN, CF 3, OCF 3, or SO 2 NR""R''"" wherein R"" and R''"" independently are hydrogen, aralkoxy, aralkyl, or C 1-6 -alkyl; or R 6 and R 7 together form an additional 4 to 7 membered ring which may be aromatic or partial saturated and which may be substituted with halogen, NO 2, CF 3, CN, OCF 3, SO 2 NR"" R""'' wherein R"" and R""'' independently are hydrogen, aralkoxy, aralkyl, or C 1-6 -alkyl, and R 4 and R 5 have the meanings set forth above, are disclosed, as well as pharmaceutical compositions thereof. Certain of the compounds are novel.The compounds and pharmaceutical compositions containing the compounds are useful in the treatment of central nervous system disorders and especially conditions sensitive to excitatory amino acids.

SEMICARBAZONES AND THIOSEMICARBAZONES OF THE HETEROCYCLIC SERIES. XLVII. ACYLATION OF ISATIN

Contrary to previous data, the acylation of isatin by carboxylic acid anhydrides in the presence of perchloric acid leads to the formation not of the O-acyl derivatives but of the N-acyl derivatives, which have a noncoplanar structure.Their transformation into isatin hydrazone and oxime is due to hydrolysis of the N-acyl group.In alcohol solutions the N-acylisatins rapidly open the five-membered ring with the addition of an alcohol molecule.