Synthesis of Curcumin Analogue, N-H and N-Benzil-4-Piperidone and their Cytotoxic Activity

Eryanti, Yum; Hendra, Rudi; Herlina, Tati; Zamri, Adel; Supratman, Unang

doi:10.1016/j.proche.2015.12.136

Cited by 4 publications

(7 citation statements)

References 5 publications

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“…This suggests a planar piperidine ring in the dienones and a sym-cis conformation present [15]. Due to the high symmetry of such molecules, the 1 H-NMR and 13 The packing diagram is shown in Fig. 2 below.…”

Section: Resultsmentioning

confidence: 96%

“…Structural similarity of 3,5-bis(arylidene)piperidin-4-one with natural curcumin [13], the main curcuminoid in turmeric root, known for its biological activity (antioxidant, antidiabetic, anti-inflammatory and anticancer, etc.) had been found.…”

Section: Resultsmentioning

confidence: 99%

“…Yield 76.1%, m.p. 135-136 °C; δ 13 The appending fluorine to the molecule of biologically active substances favorably affects bioefficiency [14]. Therefore, a directed search for novel derivatives in a series of synthetic analogs of curcumins as models/targets for compounds with a variational structure is justified.…”

Section: -(M-p-dimethoxybenzylidene-33а4567-hexah Y D R O -2 -P H E N...mentioning

confidence: 99%

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Novel 7-Aryliden-3,3a,4,5,6,7-(hexahydro-5-(2-ethoxyethyl)-2-phenyl-3-aryl-2H-pyrazolo[4,3-c]pyridine Hydrochloride: Synthesis and Structure

Koshetova¹,

Yu²,

Iskakova³

et al. 2022

Eurasian Chem. Tech. J.

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A Claisen-Schmidt type reaction of 1-(2-ethoxyethyl)piperidin-4-one with differ¬ent aromatic aldehydes led to corresponding dienones with a yield of 65‒71%. 7-Arylidene-3,3a,4,5,6,7-(hexahydro-5-(2-ethoxyethyl)-2-phenyl-3-aryl-2H-pyrazolo[4,3-c]pyridines were synthesized by heterocyclization of 3,5-dia¬rylidene-piperidin-4-ones with phenylhydrazine hydrochloride in methanol at 70 °C over 4‒6 h. The X-ray crystal structure determination of 7-(p-methoxy¬benzyliden)-3,3a,4,5,6,7-(hexahydro-5-(2-ethoxyethyl)-2-phenyl-3-(p-methoxy¬phenyl)-2H-pyrazolo[4,3-c]pyridine hydrochloride (the deposition number is CCDC 862410) was completed. The piperidine and pyrazoline rings are close to a chair and envelope conformations, respectively.

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Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

confidence: 99%

Section: -(M-p-dimethoxybenzylidene-33а4567-hexah Y D R O -2 -P H E N...mentioning

confidence: 99%

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Novel 7-Aryliden-3,3a,4,5,6,7-(hexahydro-5-(2-ethoxyethyl)-2-phenyl-3-aryl-2H-pyrazolo[4,3-c]pyridine Hydrochloride: Synthesis and Structure

Koshetova¹,

Yu²,

Iskakova³

et al. 2022

Eurasian Chem. Tech. J.

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“…Heterocyclic nuclei form the basis for the construction of numerous homological series containing hydrocarbon residues in the form of side chains, as well as various functional groups. The most important are pyrrol, pyrazole, imidazole, pyridine, pyrimidine, piperidine, furan, thiophene, indole, quinoline, purine, benzimidazole, etc (Dambaeva et al 2003;Eryanti et al 2015;Holt et al 2005;Purygin et al 2004). Heterocyclic compounds include alkaloids -nitrogen-containing physiologically active substances of plants.…”

Section: Introductionmentioning

confidence: 99%

Improvement of myelopoiesis in a cyclophosphamide-induced myelodepression model by administration of a Newly Synthesized Pyrazolo- Piperidine β-Cyclodextrine complex compound

Daulet

Baktybayeva

Belyaev

et al. 2022

Preprint

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According to WHO, the acquired secondary form of hematopoietic-depressive states increases the risk of death in people with cancer, infectious, and hormonal diseases. The choice of drugs that stimulate the proliferative activity of bone marrow cells is limited. The stimulus to the search for hematopoietic-stimulating compounds among pyridine derivatives was the manifestation of the activity of the cerebroprotective drug Mexidol (2-ethyl-6-methyl-3-hydroxypyridine succinate) to restore the granulocytes and B-lymphocytes homeostasis in clinical practice. The hematopoietic-stimulating activity of the newly synthesized compound Complex of 5-benzyl-7-(o-fluorobenzylidene)-2,3-bis(o-fluorophenyl)-3,3a,4,5,6,7-hexahydro-2H-pyrazolo [4,3-c]pyridine complex with β-cyclodextrin (BIV) was studied on a model of cyclophosphamide-induced myelodepression in C57BL6/J mouse line. The BIV compound demonstrated a stimulating effect on the process of restoring the level of Ly-6G+ Ly-6C+ granulocytes, monocytes/macrophages, CD19+ B-lymphocytes in the bone marrow, exceeding the activity of the reference drug Methyluracil. The BIV compound did not affect on the proliferative activity of c-kit (CD117+)-expressing cells, CD3e+ pre-T-lymphocytic cells and Ter-119+ erythroid cells in the bone marrow. The total number of bone marrow myelokaryocytes in the experimental groups was significantly higher than in the intact group. The pronounced hematopoietic-stimulating effect of the BIV compound gives in the future the prospect of development as a drug used for the treatment of B-lymphocytic and granulocytic-macrophage hematopoietic-depressive states.

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“…A major interest in our laboratories is the design, synthesis and antineoplastic evaluation of 1,5-diaryl-3-oxo-1,4-pentadienes mounted on a variety of scaffolds, which give rise to series 1 (Figure 1). Most previous studies of structurally-related compounds were conducted without or with very low numbers of normal cells at the same time as cancer cell lines, making it difficult to compare tumor-specificity between compounds [1][2][3][4][5][6][7][8][9][10]. Among these previous 10 papers, three papers are from our research group [5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic Tumour-Selective 1,5-Diaryl-3-Oxo-1,4-Pentadienes Mounted on a Piperidine Ring

et al. 2021

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A series of 3,5-bis(benzylidene)-4-piperidones 2a–u were prepared as candidate cytotoxic agents. In general, the compounds are highly toxic to human gingival carcinoma (Ca9-22), human squamous carcinoma-2 (HSC-2) and human squamous carcinoma-4 (HSC-4) neoplasms, but less so towards non-malignant human gingival fibroblast (HGF), human periodontal ligament fibroblast (HPLF) and human pulp cells (HPC), thereby demonstrating tumour-selective toxicity. A further study revealed that most of the compounds in series 2 were more toxic to the human Colo-205 adenocarcinoma cell line (Colo-205), human HT29 colorectal adenocarcinoma cells (HT-29) and human CEM lymphoid cells (CEM) neoplasms than towards non-malignant human foreskin Hs27 fibroblast line (Hs27) cells. The potency of the cytotoxins towards the six malignant cell lines increased as the sigma and sigma star values of the aryl substituents rose. Attempts to condense various aryl aldehydes with 2,2,6,6-tetramethyl-4-piperidone led to the isolation of some 1,5-diaryl-1,4-pentadien-3-ones. The highest specificity for oral cancer cells was displayed by 2e and 2r. In the case of 2r, its selective toxicity exceeded that of doxorubicin and melphalan. The enones 2k, m, o have the highest SI values towards colon cancer and leukemic cells. Both 2e,r inhibited mitosis and increased the subG1 population (with a transient increase in G2/M phase cells). Slight activation of caspase-3, based on the cleavage of poly(ADP-ribose)polymerase (PARP) and procaspase 3, was detected.

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Synthesis of Curcumin Analogue, N-H and N-Benzil-4-Piperidone and their Cytotoxic Activity

Cited by 4 publications

References 5 publications

Novel 7-Aryliden-3,3a,4,5,6,7-(hexahydro-5-(2-ethoxyethyl)-2-phenyl-3-aryl-2H-pyrazolo[4,3-c]pyridine Hydrochloride: Synthesis and Structure

Novel 7-Aryliden-3,3a,4,5,6,7-(hexahydro-5-(2-ethoxyethyl)-2-phenyl-3-aryl-2H-pyrazolo[4,3-c]pyridine Hydrochloride: Synthesis and Structure

Improvement of myelopoiesis in a cyclophosphamide-induced myelodepression model by administration of a Newly Synthesized Pyrazolo- Piperidine β-Cyclodextrine complex compound

Cytotoxic Tumour-Selective 1,5-Diaryl-3-Oxo-1,4-Pentadienes Mounted on a Piperidine Ring

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