An improved efficient synthesis of new N-heterocylic, homocyclic and aliphatic dronic acids

被引：0
作者：
Marooti, Shahab [1 ]
Noroozi Pesyan, Nader [2 ,3 ]
Behrouz, Somayeh [1 ]
机构：
[1] Shiraz Univ Technol, Dept Chem, Shiraz, Iran
[2] Urmia Univ, Fac Chem, Dept Organ Chem, Orumiyeh, Iran
[3] Urmia Univ, Fac Chem, Dept Organ Chem, Orumiyeh 57159, Iran
来源：
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2023年 / 198卷 / 12期
关键词：
Dronic acid; P-31; NMR; Bisphosphonate; Phosphorus acid; Carboxylic acid; Methanesulfonic acid; McLafferty rearrangement; NITROGEN-CONTAINING BISPHOSPHONATES; FATTY-ACIDS; MOLECULAR-MECHANISMS; ONE-POT; OSTEOPOROSIS; INHIBITORS; GROWTH;
D O I：
10.1080/10426507.2023.2225670
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
New N-heterocylic, homocyclic and aliphatic dronic acids were synthesized through an improved facile and versatile route by the reaction of various carboxylic acids with Phosphorus trichloride (PC), phosphorus acid (PA) and methanesulfonic acid under reflux and inert atmosphere. Representatively, the dronic acid derived from stearic acid as a long chained fatty acid was also synthesized. All the obtained compounds were analyzed and characterized by means of FT IR, H-1, C-13 and P-31 NMR spectroscopic techniques. In addition, the compound derived from stearic acid was characterized by means of FT IR and Mass spectrometry due to its insolubility in D2O and DMSO-d(6).
引用
收藏
页码：1019 / 1028
页数：10
相关论文
共 45 条
  • [1] A Mechanistic Study on the Formation of Dronic Acids
    abranyi-Balogh, Peter
    Greiner, Istvan
    Keglevich, Gyoergy
    [J]. MOLECULES, 2021, 26 (24):
  • [2] Novel structures of platinum complexes bearing N-bisphosphonates and study of their biological properties
    Alvarez-Valdes, Amparo
    Matesanz, Ana, I
    Perles, Josefina
    Fernandes, Celia
    Correia, Joao D. G.
    Mendes, Filipa
    Quiroga, Adoracion G.
    [J]. JOURNAL OF INORGANIC BIOCHEMISTRY, 2019, 191 : 112 - 118
  • [3] Bisphosphonate-Based Molecules as Potential New Antiparasitic Drugs
    Branco Santos, Joice Castelo
    de Melo, Jonathas Alves
    Maheshwari, Sweta
    Toscano Queiroz de Medeiros, Wendy Marina
    de Freitas Oliveira, Johny Wysllas
    Moreno, Claudia Jassica
    Amzel, L. Mario
    Gabelli, Sandra B.
    Silva, Marcelo Sousa
    [J]. MOLECULES, 2020, 25 (11):
  • [4] Breuer E., 2006, ANALOGUE BASED DRUG, P15
  • [5] Synthetic Procedures Leading towards Aminobisphosphonates
    Chmielewska, Ewa
    Kafarski, Pawel
    [J]. MOLECULES, 2016, 21 (11):
  • [6] Modulation of Osteoclastogenesis by Fatty Acids
    Cornish, Jillian
    MacGibbon, Alastair
    Lin, Jian-Ming
    Watson, Maureen
    Callon, Karen E.
    Tong, P. C.
    Dunford, James E.
    van der Does, Yvonne
    Williams, Garry A.
    Grey, Andrew B.
    Naot, Dorit
    Reid, Ian R.
    [J]. ENDOCRINOLOGY, 2008, 149 (11) : 5688 - 5695
  • [7] Bisphosphonates: Mechanisms of action
    Fleisch, H
    [J]. ENDOCRINE REVIEWS, 1998, 19 (01) : 80 - 100
  • [8] Effects of bisphosphonates on the growth of Entamoeba histolytica and Plasmodium species in vitro and in vivo
    Ghosh, S
    Chan, JMW
    Lea, CR
    Meints, GA
    Lewis, JC
    Tovian, ZS
    Flessner, RM
    Loftus, TC
    Bruchhaus, I
    Kendrick, H
    Croft, SL
    Kemp, RG
    Kobayashi, S
    Nozaki, T
    Oldfield, E
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (01) : 175 - 187
  • [9] On the use of 31P NMR for the quantification of hydrosoluble phosphorus-containing compounds in coral host tissues and cultured zooxanthellae
    Godinot, Claire
    Gaysinski, Marc
    Thomas, Olivier P.
    Ferrier-Pages, Christine
    Grover, Renaud
    [J]. SCIENTIFIC REPORTS, 2016, 6
  • [10] Grün A, 2015, LETT DRUG DES DISCOV, V12, P78
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