Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4-substitutedphenyl)methylene]-acetohydrazides

İnci Selin DOĞAN, (Karadeniz Teknik Üniversitesi, Eczacılık Fakültesi, Trabzon, Türkiye)
Hasan Erdinç SELLİTEPE, (Karadeniz Teknik Üniversitesi, Eczacılık Fakültesi, Trabzon, Türkiye)
Nuran KAYIKÇI, (Karadeniz Teknik Üniversitesi, Eczacılık Fakültesi, Trabzon, Türkiye)
Hande SİPAHİ, (Yeditepe Üniversitesi, Eczacılık Fakültesi, İstanbul, Türkiye)
Rengin REİS, (Yeditepe Üniversitesi, Eczacılık Fakültesi, İstanbul, Türkiye)
Nurettin YAYLI (Karadeniz Teknik Üniversitesi, Eczacılık Fakültesi, Trabzon, Türkiye)
Organic Communications
1 0
Yıl: 2018 Cilt: 11 Sayı: 3 Sayfa Aralığı: 142 - 148 Metin Dili: İngilizce DOI: 10.25135/acg.oc.47.18.06.107 İndeks Tarihi: 29-07-2022

Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4-substitutedphenyl)methylene]-acetohydrazides

Öz:
A series of five –CH3, -NO2, -OCH3 and -Cl substituted 2-hydroxy-2,2-bis(4-phenyl)-N'-[(1E)-(3/4-phenyl)methylene]acetohydrazide (1a-1e) was synthesized by the reaction of 2-hydroxy-2,2-diphenylacetohydrazidewith substituted aromatic aldehydes to give intermediate Schiff bases. Structures of the synthesized compounds werecharacterized using NMR (1D; 1H, 13C/APT and 2D 1H-1H COSY, and NOESY), FT-IR, UV, LC-MS/MS spectral dataand elemental analysis. The geometry of compounds 1a-1e were determined to be “E” by NOESY. All the testedcompounds showed cytotoxic activity on MCF-7 and PC-3 cell line at highest experimental concentration (100 μM).Compounds 1b (18.24 ± 7.62 μM) and 1e (7.62 ± 1.85 μM) have strong anti-proliferative activity on MCF-7 cell line,while compound 1b (45.81 ± 1.10 μM) has the strongest activity on PC-3 cell line.
Anahtar Kelime:

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
  • Trost, B. M.; Fleming, I. Comprehensive organic synthesis; Pergamon: New York, 1991, Vols. 1-9.
  • Sammelson, D. E.; Kurth, M. J. Carbon-carbon bond-forming solid-phase reactions. Part II, Chem. Rev. 2001, 101, 137-202. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Recent advances in the Baylis-Hillman reaction and applications. Chem. Rev. 2003, 103, 811-892.
  • Huddleston, R. R.; Krische, M. J. Enones as latent enolates in catalytic processes: Catalytic cycloreduction, cycloaddition and cycloisomerization. Synlett 2003,1, 12-21.
  • Brahmachari, G. Design for carbon-carbon bond forming reactions under ambient conditions. RSC Advances 2016, 6, 64676-64725,
  • Umehara, A., Catalytic enantioselective carbon-carbon bond forming reactions of masked acyl cyanides. J. Synth. Org. Chem. Japan 2018, 76, 255-256. Kool, E. T.; Breslow, R., Dichotomous salt effects in the hydrophobic acceleration of the benzoin condensation. J. Am. Chem. Soc. 1988, 110, 1596-1597.
  • Xin, L. H.; Potnick, J. R.; Johnson, J. S. Metallophosphites as umpolung catalysts: The enantioselective cross silyl benzoin reaction. J. Am. Chem. Soc. 2004, 126, 3070-3071.
  • Bhattacharya, A.; Purohit, V. C.; Beller, N. R. Benzoin condensation: Monitoring a chemical reaction by highpressure liquid chromatography. J. Chem. Educ. 2004, 81, 1020-1022.
  • Azizian, S.; Bafrooei, A. E.; Bashiri, H. Kinetics of catalytic oxidation of benzoin to benzil by alumina supported active MnO2, Kinet. Catal. 2010, 51, 244–249.
  • Braibante, M. E. F.; Braibante, H. T. S.; Uliana, M. P.; Costa, C. C.; Spenazzatto M. The use of benzil to obtain functionalized N-heterocycles. J. Braz. Chem. Soc. 2008, 19, 909-913.
  • Güzel, Ö.; Salman, A. Synthesis and biological evaluation of new 4-thiazolidinone derivatives. J. Enzyme Inhib. Med. Chem. 2009, 24, 1015-1023. Güzel, Ö.; İlhan, E.; Salman, A. Synthesis and antimycobacterial activity of new 2-hydroxy-N-(3-oxo-1-thia- 4-azaspiro[4.4]non-4-yl)/(3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-2,2-diphenyl-acetamid derivatives. Monatsh. Chem. 2006, 137, 795-801.
  • Safieh, K. A. A.; Al-Titi, A. M. S.; Zahra, J. A.; Ayoub M. T. Oxidative cyclization of arylidene carboxyhydrazides: Synthesis of substituted hydroxydiphenylmethyl-1,3,4-oxadiazoles. Jordan J. Chem. 2007, 2, 211-218.
  • Rollas, S.; Buyuktimkin, S.; Buyuktimkin, N.; Ulgen, M.; Yemni, E. Evaluation of some arylhydrazones of benzilic acid as antimicrobial agents. Pharmazie 1988, 43, 511-511.
  • Fahmy, H. T. Y. Synthesis of some new triazoles as potential antifungal agents. Boll. Chim. Farmaco 2001, 140, 422–427.
  • Rao, A.; Carbone. A.; Chimirri, A.; De Clercq, E.; Monforte, A. M.; Monforte, P.; Pannecouque, C.; Zappalá, M. Synthesis and anti-HIV activity of 2,3-diaryl-1,3-thiazolidin-4-(thi)one derivatives. Farmaco 2002, 57, 747-751.
  • Rao, A.; Balzarini, J.; Carbone, A.; Chimirri, A.; De Clercq, E.; Luca, L. D.; Monforte, A. M.; Monforte, P.; Pannecouque, C.; Zappalá, M. Synthesis of new 2,3-diaryl-1,3-thiazolidin-4-ones as anti-HIV agents. Farmaco 2004, 59, 33-39.
  • Barreca, M. L.; Chimirri, A.; Luca L. D.; Monforte, A. M.; Monforte, P.; Rao, M.; Zappalá, M.; Balzarini, J.; De Clercq, E.; Pannecouque, C.; Witvrouw, P. Discovery of 2,3-diaryl-1,3-thiazolidin-4-ones as potent anti- HIV agents. Bioorg. Med. Chem. Lett. 2001, 11, 1793-1796.
  • Barreca, M. L.; Chimirri, A.; De Clercq, E.; Luca, L. D.; Monforte, A. M.; Monforte, P.; Rao, A.; Zappalá, M. Design and discovery of new potent RT inhibitors. Farmaco 2003, 58, 259-263.
  • Rao, A.; Carbone, A.; Chimirri, A.; De Clercq, E.; Monforte, A. M.; Monforte, P.; Pannecouque, C.; Zappalá, M. Synthesis and anti-HIV activity of 2,3-diaryl-1,3-thiazolidin-4-ones. Farmaco 2003, 58, 115-120.
  • Ragab, F. A.; Eid, N. M.; El-Tawab, H. A. Synthesis and anticonvulsant activity of new thiazolidinone and thioxoimidazolidinone derivatives derived from furochromones. Pharmazie 1997, 52, 926-929.
  • Babaoglu, K.; Page, M. A.; Jones, V. C.; McNeil, M.; Dong, C.; Naismith, J. H.; Lee, R. E. Novel inhibitors of an emerging target in Mycobacterium tuberculosis; substituted thiazolidinones as inhibitors of dTDPrhamnose synthesis. Bioorg. Med. Chem. Lett. 2003, 13, 3227-3230.
  • Bukowski, L.; Janowiec, M.; Zwolska-Kwiek, Z.; Andrezejczyk, Z. Some reactions of 2-cyanomethylimidazo[4,5-b]pyridine with isothiocyanates. Antituberculotic activity of the obtained compounds. Pharmazie 1998, 53, 373-376.
  • Srivastava, T.; Gaikwad, A. K.; Haq, W.; Sinha, S.; Kati, S. B. Synthesis and biological evaluation of 4- thiazolidinone derivatives as potential antimycobacterial agents. Arkivoc 2005, ii, 120-130.
  • Çoruh, I.; Rollas, S., Turan, S. Ö.; Akbuğa, J. Synthesis and evaluation of cytotoxic activities of some 1,4- disubstituted thiosemicarbazides, 2,5-disubstituted-1,3,4-thiadiazoles and 1,2,4-triazole-5-thiones derived from benzilic acid hydrazide. Marmara Pharm. J. 2012, 16, 56-63.
  • Karali, N.; İlhan, E.; Gürsoy, A.; Kiraz, M. New cyclohexlidenehydrazide and 4-aza-1-thiaspiro[4,5]decan-3- one derivatives of 3-phenyl-4(3H)-quinazolinones. Farmaco 1998, 53, 346-349.
  • Taha, M.; Shah, S. A. A.; Afifi, M.; Zulkeflee, M.; Sultan, S.; Wadood, A.; Rahim, F.; Ismail, N. H. Morpholine hydrazone scaffold: Synthesis, anticancer activity and docking studies. Chin. Chem. Lett. 2017, 28, 607-611.
  • Rodriguesa, B. S.; Ávilaa, R. I.; Benficaa, P. L.; Bringelb, L. P.; Oliveirab, C. M. A.; Vandresenc, F.; Silvad, C. C.; Valadaresa, M. C. 4-Fluorobenzaldehyde limonene-based thiosemicarbazone induces apoptosis in PC-3 human prostate cancer cells. Life Sci. 2018, 203, 141-149.
APA DOGAN I, SELLİTEPE H, Kayıkçı N, Sipahi H, Reis R, YAYLI N (2018). Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4-substitutedphenyl)methylene]-acetohydrazides. , 142 - 148. 10.25135/acg.oc.47.18.06.107
Chicago DOGAN INCI SELIN,SELLİTEPE Hasan Erdinç,Kayıkçı Nuran,Sipahi Hande,Reis Rengin,YAYLI Nurettin Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4-substitutedphenyl)methylene]-acetohydrazides. (2018): 142 - 148. 10.25135/acg.oc.47.18.06.107
MLA DOGAN INCI SELIN,SELLİTEPE Hasan Erdinç,Kayıkçı Nuran,Sipahi Hande,Reis Rengin,YAYLI Nurettin Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4-substitutedphenyl)methylene]-acetohydrazides. , 2018, ss.142 - 148. 10.25135/acg.oc.47.18.06.107
AMA DOGAN I,SELLİTEPE H,Kayıkçı N,Sipahi H,Reis R,YAYLI N Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4-substitutedphenyl)methylene]-acetohydrazides. . 2018; 142 - 148. 10.25135/acg.oc.47.18.06.107
Vancouver DOGAN I,SELLİTEPE H,Kayıkçı N,Sipahi H,Reis R,YAYLI N Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4-substitutedphenyl)methylene]-acetohydrazides. . 2018; 142 - 148. 10.25135/acg.oc.47.18.06.107
IEEE DOGAN I,SELLİTEPE H,Kayıkçı N,Sipahi H,Reis R,YAYLI N "Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4-substitutedphenyl)methylene]-acetohydrazides." , ss.142 - 148, 2018. 10.25135/acg.oc.47.18.06.107
ISNAD DOGAN, INCI SELIN vd. "Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4-substitutedphenyl)methylene]-acetohydrazides". (2018), 142-148. https://doi.org/10.25135/acg.oc.47.18.06.107
APA DOGAN I, SELLİTEPE H, Kayıkçı N, Sipahi H, Reis R, YAYLI N (2018). Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4-substitutedphenyl)methylene]-acetohydrazides. Organic Communications, 11(3), 142 - 148. 10.25135/acg.oc.47.18.06.107
Chicago DOGAN INCI SELIN,SELLİTEPE Hasan Erdinç,Kayıkçı Nuran,Sipahi Hande,Reis Rengin,YAYLI Nurettin Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4-substitutedphenyl)methylene]-acetohydrazides. Organic Communications 11, no.3 (2018): 142 - 148. 10.25135/acg.oc.47.18.06.107
MLA DOGAN INCI SELIN,SELLİTEPE Hasan Erdinç,Kayıkçı Nuran,Sipahi Hande,Reis Rengin,YAYLI Nurettin Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4-substitutedphenyl)methylene]-acetohydrazides. Organic Communications, vol.11, no.3, 2018, ss.142 - 148. 10.25135/acg.oc.47.18.06.107
AMA DOGAN I,SELLİTEPE H,Kayıkçı N,Sipahi H,Reis R,YAYLI N Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4-substitutedphenyl)methylene]-acetohydrazides. Organic Communications. 2018; 11(3): 142 - 148. 10.25135/acg.oc.47.18.06.107
Vancouver DOGAN I,SELLİTEPE H,Kayıkçı N,Sipahi H,Reis R,YAYLI N Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4-substitutedphenyl)methylene]-acetohydrazides. Organic Communications. 2018; 11(3): 142 - 148. 10.25135/acg.oc.47.18.06.107
IEEE DOGAN I,SELLİTEPE H,Kayıkçı N,Sipahi H,Reis R,YAYLI N "Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4-substitutedphenyl)methylene]-acetohydrazides." Organic Communications, 11, ss.142 - 148, 2018. 10.25135/acg.oc.47.18.06.107
ISNAD DOGAN, INCI SELIN vd. "Synthesis and anticancer (MCF-7, PC-3) activities of new 2-hydroxy-2,2-bis(4-substitutedphenyl)-N'-[(1E)-(3/4-substitutedphenyl)methylene]-acetohydrazides". Organic Communications 11/3 (2018), 142-148. https://doi.org/10.25135/acg.oc.47.18.06.107
Sayfa Oluşturulma Tarihi
23-04-2024 13:52

İLETİŞİM

TÜBİTAK ULAKBİM TR Dizin

Yüzüncüyıl, İşçi Blokları Mahallesi

Muhsin Yazıcıoğlu Caddesi No:51/C

06530 Çankaya / ANKARA +90 (312) 298 92 00

trdizin@tubitak.gov.tr

TÜBİTAK ULAKBİM Ulusal Akademik Ağ ve Bilgi Merkezi Cahit Arf Bilgi Merkezi © Tüm Hakları Saklıdır. Gizlilik Politikası Kullanım Şartları