Efficient one-pot, three-component procedure to prepare new α-aminophosphonate and phosphonic acid acyclic nucleosides

被引：13
作者：
Baddi, Laila [1 ]
Ouzebla, Driss [1 ]
El Mansouri, Az-Eddine [1 ]
Smietana, Michael [2 ]
Vasseur, Jean-Jacques [2 ]
Lazrek, Hassan B. [1 ]
机构：
[1] Cadi Ayyad Univ, Fac Sci Semlalia, Unite Chim Biomol & Med, Lab Chim Biomol, Marrakech 40000, Morocco
[2] Univ Montpellier II, Inst Biomol Max Mousseron, UMR CNRS UMI UMII 5247, Montpellier, France
来源：
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2021年 / 40卷 / 01期
关键词：
Acyclic nucleosides; alpha-aminophosphonates; Kabachnik-Fields reaction; catalysis; natural phosphate; DOPED NATURAL PHOSPHATE; SOLVENT-FREE CONDITIONS; AMINO PHOSPHONATES; CARBONYL-COMPOUNDS; FACILE SYNTHESIS; INHIBITORS; DERIVATIVES; IODINE; DESIGN; PROTECTION;
D O I：
10.1080/15257770.2020.1826516
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
An efficient one-pot three-component Kabachnik-Fields reaction of aldehydes (acyclic nucleosides), amines (or amino acid), and triethyl phosphite proceeded for the synthesis of aminophosphonates using natural phosphate coated with iodine (I-2@NP) as a catalyst. The novel alpha-aminophosphonate and phosphonic acid acyclic nucleosides were tested for their anti-HCV and anti-HIV activities. The molecular docking showed that the non-activity of these compounds could be due to the absence of hydrophobic pharmacophores.
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页码：43 / 67
页数：25
相关论文
共 56 条
[1]   RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND [J].
ALLEN, MC ;
FUHRER, W ;
TUCK, B ;
WADE, R ;
WOOD, JM .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1652-1661
[2]   One-pot synthesis of α-aminophosphonates catalyzed by antimony trichloride adsorbed on alumina [J].
Ambica ;
Kumar, Satish ;
Taneja, Subhash C. ;
Hundal, Maninder S. ;
Kapoor, Kamal K. .
TETRAHEDRON LETTERS, 2008, 49 (14) :2208-2212
[3]   SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF ANTIBACTERIAL PHOSPHONOPEPTIDES INCORPORATING (1-AMINOETHYL)PHOSPHONIC ACID AND (AMINOMETHYL)PHOSPHONIC ACID [J].
ATHERTON, FR ;
HASSALL, CH ;
LAMBERT, RW .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (01) :29-40
[4]   A mild and highly efficient protocol for the one-pot synthesis of primary α-amino phosphonates under solvent-free conditions [J].
Azizi, N ;
Rajabi, F ;
Saidi, MR .
TETRAHEDRON LETTERS, 2004, 45 (50) :9233-9236
[5]   Catalysis by phosphates: A simple and efficient procedure for transesterification reaction [J].
Bazi, Fathallaah ;
El Badaoui, Hanane ;
Tamani, Soumia ;
Sokori, Samira ;
Oubella, Latifa ;
Hamza, Mohamed ;
Boulaajaj, Said ;
Sebti, Said .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 256 (1-2) :43-47
[6]   Three component coupling catalyzed by TaCl5-SiO2:: synthesis of α-amino phosphonates [J].
Chandrasekhar, S ;
Prakash, SJ ;
Jagadeshwar, V ;
Narsihmulu, C .
TETRAHEDRON LETTERS, 2001, 42 (32) :5561-5563
[7]   Synthesis and herbicidal activity evaluation of novel α-amino phosphonate derivatives containing a uracil moiety [J].
Che, Jian-yi ;
Xu, Xiao-yun ;
Tang, Zi-long ;
Gu, Yu-cheng ;
Shi, De-qing .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (04) :1310-1313
[8]   Synthesis and Biological Activity Evaluation of Novel α-Amino Phosphonate Derivatives Containing a Pyrimidinyl Moiety as Potential Herbicidal Agents [J].
Chen, Jin-Long ;
Tang, Wu ;
Che, Jian-Yi ;
Chen, Kai ;
Yan, Gang ;
Gu, Yu-Cheng ;
Shi, De-Qing .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2015, 63 (32) :7219-7229
[9]  
Cherkasov R. A., 1998, RUSS CHEM REV, V67, P857, DOI DOI 10.1070/RC1998V067N10ABEH000421
[10]   New Efavirenz Derivatives and 1,2,3-Triazolyl-phosphonates as Inhibitors of Reverse Transcriptase of HIV-1 [J].
Costa, Carolina C. P. ;
Boechat, Nubia ;
Bastos, Monica M. ;
da Silva, Fernando de C. ;
Marttorelli, Andressa ;
Souza, Thiago M. L. ;
Baptista, Mayara S. ;
Hoelz, Lucas V. B. ;
Cafffarena, Ernesto R. .
CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2018, 18 (17) :1494-1505
123456