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I. NUCLEOSIDES: Biological Activity

Hept Derivatives: 6-Benzyl-1-ethoxymethyl-5-isopropyluracil (MKC-442)

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Pages 575-583 | Published online: 16 Feb 2007

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Galal H. Elgemeie, Sheikha A. Alkhursani & Reham A. Mohamed. (2019) New synthetic strategies for acyclic and cyclic pyrimidinethione nucleosides and their analogues. Nucleosides, Nucleotides & Nucleic Acids 38:1, pages 12-87.
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Ahmed F. Khattab. (2006) Synthesis of New 5‐Substituted Pyrimidine Acyclonucleosides. Synthetic Communications 36:8, pages 1097-1107.
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IbrahimF. Zeid, AdelA: H. Abdel-Rahman, AhmedE.-S. Abdel-Megied & Abd-Allah Sh. Ei-Etrawy. (1999) Synthesis of New Thiolated Acyclonucleosides with Potential Anti-HBV Activity. Nucleosides and Nucleotides 18:1, pages 95-111.
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Qing-Qing Hao, Xiao-Mei Chen, Christophe Pannecouque, Erik De Clercq, Shuai Wang & Fen-Er Chen. (2023) Structure-directed linker optimization of novel HEPTs as non-nucleoside inhibitors of HIV-1 reverse transcriptase. Bioorganic Chemistry 133, pages 106413.
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S. P. Gasparyan, M. V. Alexanyan, G. K. Arutyunyan, S. L. Kocharov, A. H. Martirosyan, R. A. Tamazyan, A. G. Ayvazyan, H. A. Panosyan & G. G. Danagulyan. (2017) Synthesis of new derivatives of 5-(3,4-dihydro-2Н-pyrrol-5-yl)-pyrimidine. Russian Journal of Organic Chemistry 52:11, pages 1646-1653.
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I. A. Novakov, M. B. Navrotskii, E. K. Zakharova & L. L. Brunilina. (2016) C(2)-Functionalization of pyrimidin-4(3H)-one derivatives in the synthesis of its biologically active derivatives. Russian Chemical Bulletin 64:11, pages 2545-2561.
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Li Li, Liying Ma, Xiaowei Wang & Junyi Liu. (2013) New Efficient and Flexible Synthetic Route to Emivirine and Its Analogs. Journal of Heterocyclic Chemistry 50:1, pages 164-168.
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Xiaowei Wang, Jianfang Zhang, Yang Huang, Ruiping Wang, Liang Zhang, Kang Qiao, Li Li, Chang Liu, Yabo Ouyang, Weisi Xu, Zhili Zhang, Liangren Zhang, Yiming Shao, Shibo Jiang, Liying Ma & Junyi Liu. (2012) Design, Synthesis, and Biological Evaluation of 1-[(2-Benzyloxyl/alkoxyl)methyl]-5-halo-6-aryluracils as Potent HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors with an Improved Drug Resistance Profile. Journal of Medicinal Chemistry 55:5, pages 2242-2250.
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Mariela Bollini, Robert A. Domaoal, Vinay V. Thakur, Ricardo Gallardo-Macias, Krasimir A. Spasov, Karen S. Anderson & William L. Jorgensen. (2011) Computationally-Guided Optimization of a Docking Hit to Yield Catechol Diethers as Potent Anti-HIV Agents. Journal of Medicinal Chemistry 54:24, pages 8582-8591.
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Hua Qin, Chang Liu, Ying Guo, Ruiping Wang, Jianfang Zhang, Liying Ma, Zhili Zhang, Xiaowei Wang, Yuxin Cui & Junyi Liu. (2010) Synthesis and biological evaluation of novel C5 halogen-functionalized S-DABO as potent HIV-1 non-nucleoside reverse transcriptase inhibitors. Bioorganic & Medicinal Chemistry 18:9, pages 3231-3237.
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Tatjana Gazivoda Kraljević, Svjetlana Krištafor, Lidija Šuman, Marijeta Kralj, Simon M. Ametamey, Mario Cetina & Silvana Raić-Malić. (2010) Synthesis, X-ray crystal structure study and antitumoral evaluations of 5,6-disubstituted pyrimidine derivatives. Bioorganic & Medicinal Chemistry 18:7, pages 2704-2712.
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Tatjana Gazivoda, Svjetlana Krištafor, Mario Cetina, Ante Nagl & Silvana Raić-Malić. (2008) Synthesis and structural studies of C-5 aryl- and C-6 alkyl-substituted pyrimidine derivatives. Structural Chemistry 19:3, pages 441-449.
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A. I. Rakhimov, E. S. Titova, R. G. Fedunov & V. A. Babkin. (2008) Special features of the nucleophilic substitution of halogen in alkyl and benzyl halides with anions generated from 4-hydroxy-2-mercapto-6-methylpyrimidine. Chemistry of Heterocyclic Compounds 44:6, pages 700-708.
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Frans Therkelsen, Per T. Jørgensen, Claus Nielsen & Erik B. Pedersen. (2007) New Emivirine (MKC-442) Analogues Containing a Tetrahydronaphthalene at C-6 and their Anti-HIV Activity. Monatshefte für Chemie - Chemical Monthly 138:5, pages 495-503.
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Youssef L. Aly, Erik B. Pedersen, Paolo La Colla & Roberta Loddo. (2007) Synthesis and Anti‐HIV‐1 Activity of New MKC‐442 Analogues with an Alkynyl‐Substituted 6‐Benzyl Group*. Archiv der Pharmazie 340:5, pages 225-235.
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Youssef L. Aly, Erik B. Pedersen, Paolo La Colla & Roberta Loddo. (2007) Synthesis and anti-HIV-1 activity of 1,3-phenylene bis-uracil analogues of MKC-442. Journal of Heterocyclic Chemistry 44:2, pages 381-387.
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A. I. Rakhimov & E. S. Titova. (2007) Synthesis of 2-alkyl(aralkyl)sulfanyl-6-methylpyrimidin-4(3H)-ones and 4-alkyl(aralkyl)oxy-2-alkyl(aralkyl)sulfanyl-6-methylpyrimidines. Russian Journal of Organic Chemistry 43:1, pages 96-102.
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Nasser R. El‐Brollosy. (2009) Synthesis of novel quinazoline non‐nucleosides analogues of the HIV drug emivirine. Journal of Heterocyclic Chemistry 43:6, pages 1435-1440.
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Xiaowei Wang, Qinghua Lou, Ying Guo, Yang Xu, Zhili Zhang & Junyi Liu. (2006) The design and synthesis of 9-phenylcyclohepta[d]pyrimidine-2,4-dione derivatives as potent non-nucleoside inhibitors of HIV reverse transcriptase. Organic & Biomolecular Chemistry 4:17, pages 3252.
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Michael Wamberg, Erik B. Pedersen, Nasser R. El-Brollosy & Claus Nielsen. (2004) Synthesis of 6-arylvinyl analogues of the HIV drugs SJ-3366 and Emivirine. Bioorganic & Medicinal Chemistry 12:5, pages 1141-1149.
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Farag A. El‐Essawy, Nasser R. El‐Brollosy, Erik B. Pedersen & Claus Nielsen. (2009) Synthesis of new uracil non‐nucleoside derivatives as potential inhibitors of HIV‐1. Journal of Heterocyclic Chemistry 40:2, pages 213-217.
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Raffaele Saladino, Umberto Ciambecchini, Giovanni Maga, Paola Mastromarino, Cinzia Conti & Maurizio Botta. (2002) A new and efficient synthesis of substituted 6-[(2′-Dialkylamino)ethyl] pyrimidine and 4- N,N -Dialkyl-6-vinyl-cytosine derivatives and evaluation of their anti-Rubella activity. Bioorganic & Medicinal Chemistry 10:7, pages 2143-2153.
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Maurizio Botta, Federico Corelli, Giovanni Maga, Fabrizio Manetti, Michela Renzulli & Silvio Spadari. (2001) Research on anti-HIV-1 agents. Part 2: Solid-phase synthesis, biological evaluation and molecular modeling studies of 2,5,6-trisubstituted-4(3H)-pyrimidinones targeting HIV-1 reverse transcriptase. Tetrahedron 57:39, pages 8357-8367.
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Maurizio Botta, Francesca Occhionero, Rosario Nicoletti, Paola Mastromarino, Cinzia Conti, Maurizio Magrini & Raffaele Saladino. (1999) Synthesis and biological evaluation of 2-methoxy- and 2-Methylthio-6-[(2′-alkylamino)ethyl]-4(3 H )-pyrimidinones with anti-rubella virus activity. Bioorganic & Medicinal Chemistry 7:9, pages 1925-1931.
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Hiromichi Tanaka, Hiroyuki Hayakawa, Kazuhiro Haraguchi, Tadashi Miyasaka, Richard T. Walker, E. De Clercq, Masanori Baba, David K. Stammers & David I. Stuart. 1999. 93 144 .
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Mika Okamoto, Masahiko Makino, Kazunori Yamada, Kouji Nakade, Satoshi Yuasa & Masanori Baba. (1996) Complete inhibition of viral breakthrough by combination of MKC-442 with AZT during a long-term culture of HIV-1-infected cells. Antiviral Research 31:1-2, pages 69-77.
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M. BABA, H. TANAKA, T. MIYASAKA, S. YUASA, M. UBASAWA, R. T. WALKER & E. DE CLERCQ. (2010) ChemInform Abstract: HEPT Derivatives: 6‐Benzyl‐1‐ethoxymethyl‐5‐isopropyluracil (MKC‐442).. ChemInform 26:40.
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John M. Gardiner & Colin R. Loyns. (1995) Synthesis of novel 1-, 1,4- and 1,7-substituted 2-mercapto- and 2-methylmercapto- benzimidazoles: Acyclic analogues of the HIV-1 RT inhibitor, TIBO. Tetrahedron 51:42, pages 11515-11530.
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