458
J. L. Viveros-Ceballos et al.
Ho B, Crider AM, Stables JP (2001) Synthesis and structure-activity
relationships of potential anticonvulsants based on 2-piperidine-
carboxylic acid and related pharmacophores. Eur J Med Chem
36:265–286
Informed consent No experiments involving living things were per-
formed so informed consent is not required.
Imani Z, Mundlapati VR, Goldsztejn G, Brenner V, Gloaguen E, Guil-
lot R, Baltaze JP, Barbu-Debus KL, Robin S, Zehnacker A, Mons
M, Aitken DJ (2020) Conformation control through concurrent
N-H⋯S and N–H⋯O=C hydrogen bonding and hyperconjugation
efects. Chem Sci 11:9191–9197
References
Aldrich JV, McLaughlin JP (2012) Opioid peptides: potential for drug
development. Drug Discov Today Technol 9:23–31
Jiménez-Andreu MM, Sayago FJ, Cativiela C (2018) An improved
synthesis of the antibiotic dehydrophos. Eur J Org Chem
2018:3965–3973
Almansour AI, Kumar RS, Arumugam N, Bianchini G, Menéndez JC,
Al-thamili DM, Periyasami G, Altaf M (2019) Design and syn-
thesis of A- and D ring-modifed analogues of luotonin A with
reduced planarity. Tetrahedron Lett 60:1514–1517
Kantoci D, Denike JK, Wechter WJ (1996) Synthesis of aminobispho-
sphonate. Synth Commun 26:2037–2043
Argüello-Velasco RO, Dziuk B, Zarychta B, Ordóñez M, Kafarski
P (2019a) Reactions of piperazin-2-one, morpholin-3-one, and
thiomorpholin-3-one with triethyl phosphite prompted by phos-
phoryl chloride: scope and limitations. ACS Omega 4:9056–9064
Argüello-Velasco RO, Sánchez-Muñoz GK, Viveros-Ceballos JL,
Ordóñez M, Kafarski K (2019b) A straightforward synthesis of
six-membered-ring heterocyclic α-aminophosphonic acids from
N-acyliminium ions. J Het Chem 56:2068–2073
Klutchko S, Blankley CJ, Fleming RW, Hinkley JM, Werner AE, Nor-
din I, Holmes A, Hoefe ML, Cohen DM, Essenburg AD, Kaplan
HR (1986) Synthesis of novel angiotensin converting enzyme
inhibitor quinapril and related compounds. A divergence of
structure-activity relationships for non-sulfhydryl and sulfhydryl
types. J Med Chem 29:1953–1961
Kotha S, Deodhar D, Khedkar P (2014) Diversity-oriented synthesis
of medicinally important 1,2,3,4-tetrahydroisoquinoline-3-carbox-
ylic acid (Tic) derivatives and higher analogs. Org Biomol Chem
12:9054–9091
Bentley DJ, Slawin AMZ, Moody CJ (2006) Total synthesis of stepha-
notic acid methyl ester. Org Lett 8:1975–1978
Berezowska I, Chung NN, Lemieux C, Wilkes BC, Schiller PW (2009)
Agonist vs antagonist behavior of δ opioid peptides containing
novel phenylalanine analogues in place of Tyr1. J Med Chem
52:6941–6945
Kotha S, Chavan AS, Goyal D (2019) Diversity-oriented approaches to
polycycles and heterocycles via enyne metathesis and Diels-Alder
reaction as key steps. ACS Omega 4:22261–22273
Kubícek V, Rudovský J, Kotek J, Hermann P, Elst LV, Muller RN,
Kolar ZI, Wolterbeek HT, Peters JA, Lukes I (2005) A bispho-
sphonate monoamide analogue of DOTA: a potential agent for
bone targeting. J Am Chem Soc 127:16477–16485
Bidar M, Tokmajyan G, Nasiri F (2013) Selective reduction of unsat-
urated γ- and δ-lactones by magnesium-methanol. Chem Nat
Compd 48:942–945
Borase BB, Godbole HM, Singh GP, Upadhyay PR, Trivedi A, Bhat
V, Shenoy GG (2020) Application of Ugi three component reac-
tion for the synthesis of quinapril hydrochloride. Synth Commun
50:48–55
Lee EJ, Choi MJ, Lee G, Gaire BP, Choi JW, Kim HS (2017) Regula-
tion of neuroinfammation by matrix metalloproteinase-8 inhibi-
tor derivatives in activated microglia and astrocytes. Oncotarget
8:78677–78690
Boto A, Gallardo JA, Hernández R, Saavedra CJ (2005a) One-pot syn-
thesis of α-amino phosphonates from α-amino acids and β-amino
alcohols. Tetrahedron Lett 46:7807–7811
Leftheris K, Kline T, Vite GD, Cho YH, Bhide RS, Patel DV, Patel
MM, Schmidt RJ, Weller HN, Andahazy ML, Carboni JM, Gullo-
Brown JL, Lee FYF, Ricca C, Rose WC, Yan N, Barbacid M,
Hunt JT, Meyers CA, Seizinger BR, Zahler R, Manne V (1996)
Development of highly potent inhibitors of Ras farnesyltransferase
possessing cellular and in vivo activity. J Med Chem 39:224–236
Lejczak B, Kafarski P (2009) Biological activity of aminophosphonic
acids and their short peptides. Top Heterocycl Chem 20:31–63
Maryanof BE, Zhang HC, Cohen JH, Turchi IJ, Maryanof CA (2004)
Cyclizations of N-acyliminium ions. Chem Rev 104:1431–1628
Matter H, Schudok M, Schwab W, Thorwart W, Barbier D, Billen G,
Haase B, Neises B, Weithmann KU, Wollmann T (2002) Tetrahy-
droisoquinoline-3-carboxylate based matrix-metalloproteinase
inhibitors: design, synthesis and structure-activity relationship.
Bioorg Med Chem 10:3529–3544
Boto A, Hernández R, de León Y, Gallardo JA (2005b) Synthesis of
alkaloid analogues from α-amino acids by one-pot radical decar-
boxylation/alkylation. Eur J Org Chem 2005:3461–3468
Burckhalter JH, Stephens VC (1951) Synthesis of phenylalanine ana-
logs as antimetabolites. J Am Chem Soc 73:56–58
Chrzanowska M, Grajewska A, Rozwadowska MD (2016) Asymmet-
ric synthesis of isoquinoline alkaloids: 2004–2015. Chem Rev
116:12369–12465
Dabrowska E, Burzynska A, Mucha A, Matczak-Jon E, Sawka-
Dobrowolska W, Berlicki L, Kafarski P (2009) Insight into the
mechanism of three component condensation leading to amino-
methylenebisphosphonates. J Organomet Chem 694:3806–3813
de Joncheere CP (2020) Precursors and chemicals frequently used in
the illicit manufacture of narcotic drugs and psychotropic sub-
stances 2019. International Narcotic Control Board, Vienna
Gluza K, Kafarski P (2013) Transition state analogues of enzymatic
reaction as potential drugs. In: El-Shemy H (ed) Drug discovery,
1st edn. InTech, Rijeka, pp 325–372
Milanos L, Brox R, Frank T, Poklukar G, Palmisano R, Waibel R, Ein-
siedel J, Dürr M, Ivanovic-Burmazovic I, Larsen O, Hjorto GM,
Rosenkilde MM, Tschammer N (2016) Discovery and charac-
terization of biased allosteric agonists of the chemokine receptor
CXCR3. J Med Chem 59:2222–2243
Modarresi-Alam AR, Najaf P, Rostamizadeh M, Keykha H, Bijan-
Hartung J, Gottwald T, Spehar K (2002) Selectivity in the chemistry of
oxygen-centered radicals—the formation of carbon-oxygen bonds.
Synthesis 2002:1469–1498
zadeh HR, Kleinpeter E (2007) Dynamic 1
H NMR study of the
barrier to rotation about the C-N bond in primary carbamates and
its solvent dependence. J Org Chem 72:2208–2211
Hayashi K, Ozaki Y, Nunami K, Yoneda N (1983) Facile preparation
of optically pure (3S)- and (3R)-1,2,3,4-tetrahydroisoquinoline-
3-carboxylic acid. Chem Pharm Bull 31:312–314
Mucha A, Kafarski P, Berlicki L (2011) Remarkable potential of the
α-aminophosphonate/phosphinate structural motif in medicinal
chemistry. J Med Chem 54:5955–5980
Hernández-Moreno JT, Romero-Estudillo I, Cativiela C, Ordóñez
M (2020) Practical synthesis of 1,2,3,4-tetrahydroisoquinoline-
1-phosphonic and 1-phosphinic acids through Kabachnik-Fields
and Aza-Pudovik Reaction. Synthesis 52:769–774
Murashkina AV, Mitrofanov AY, Grishin YK, Rybakov VB, Belets-
kaya IP (2018) Convenient Au(III)-catalysed synthesis of 1-alkyl-
3-diethoxy-phosphoryl-1,2,3,4-tetrahydroisoquinolines. Chem Sel
3:6810–6813
1 3