Amino analogs of echinochrome and ethylmompain, metabolites of sea urchins Scaphechinus mirabilis and Echinothrix diadema, and amino analogs of cristazarin, a metabolite of lichen Cladonia cristatella, were synthesized.
ThomsonRH. (1971) Naturally Occurring Quinones, 2nd Ed. Academic Press, London, New York, p.734;
2.
(1987) 3nd ed., Chapman and Hall London, New York, p.732;
3.
(1997) 4th, Blackie Academic and Professional, Londom, New York, p.746.
4.
MischenkoNP, FedoreyevSA, PokhiloND, AnufrievVP, DenisenkoVA, GlazunovVP. (2005) Echinamines A and B, first aminated hydroxynaphthazarins from the sea urchin Scaphechinus mirabilis. Journal of Natural Products, 68, 1390–1393.
5.
ZhouDY, QinL, ZhuBW, WangXD, TanH, YangJF, LiDM, DongXP, WuHT, SunLM, LiXL, MurataY. (2011) Extraction and antioxidant property of polyhydroxylated naphthoquinone pigments from spines of purple sea urchin Strongylocentrotus nudus. Food Chemistry, 129, 1591–1597.
6.
PowellC, HughesAD, KellyMS, ConnerS, McDougallGJ. (2014) Extraction and identification of antioxidant polyhydroxynaphthoquinone pigments from the sea urchin, Psammechinus miliaris. LWT – Food Science and Technology, 59, 455–460.
7.
VasilevaEA, MischenkoNP, ZadorozhnyPA, FedoreyevSA. (2016) New aminonaphthoquinone from the sea urchin Strongylocentrotus pallidus and Mesocentrotus nudus. Natural Product Communications, 11, 821–824.
8.
PokhiloND, ShuvalovaMI, LebedkoMV, SopelnyakGI, YakubovskayaAYa, MischenkoNP, FedoreyevSA, AnufrievVP. (2006) Synthesis of echinamines A and B, the first aminated hydroxynaphthazarins produced by the sea urchin Scaphechinus mirabilis and its analogues. Journal of Natural Products, 69, 1125–1129.
9.
PokhiloND, YakubovskayaA.Y, DenisenkoVA, AnufrievVP. (2006) Regiospecificity in the reaction of 2,3-dichloronaphthazarins with azide anions. Synthesis of echinamine A – a metabolite produced by the sea urchin Scaphechinus mirabilis. Tetrahedron Letters, 47, 1385–1387.
10.
MelmanGI, BorisovaKL, PokhiloND, MakhankovVV, AnufrievVP. (2016) Unexpected conversion of echinochrome to brominated spinochrome D. Synthesis of 2-amino-3,6,7-trihydroxynaphthazarin produced by the sea urchins Strongylocentrotus nudus and Psammechinus miliaris. Tetrahedron Letters, 57, 736–738.
11.
CouladourosEA, PlytaZF, HaroutounianSA, PapageorgiouVP. (1997) Efficient synthesis of aminonaphthoquinones and azidobenzohydroquinones: mechanistic considerations of the reaction of hydrazoic acid with quinones. An overview. The Journal of Organic Chemistry, 62, 6–10.
12.
AnufrievVP, TchizhovaAY, DenisenkoVA, NovikovVL. (1993) The chemistry of naphthazarin derivatives. I. Reactions of 2-hydroxynaphthazarins with saturated aldehydes. Russian Journal of Organic Chemistry, 29, 2008–2017.
13.
YamamotoY, MatsubaraH, KinoshitaY, KinoshitaK, KoyamaK, TakahashiK, AhmadjiamV, KurokawaT, YoshimuraI. (1996) Naphthazarin derivatives from cultures of the lichen Cladonia cristatella. Phytochemistry, 43, 1239–1242.
14.
MooreRE, SinghH, ScheuerPJ. (1966) Isolation of eleven new spinochromes from Echinoids of the genus Echinothrix. Journal of Organic Chemistry, 31, 3645–3650.
15.
PokhiloND, MelmanGI, KiselevaMI, DenisenkoVA, AnufrievVP. (2015) Synthesis, cytotoxic and contraceptive activity of 6,8,9-trihydroxy-2-methyl-2H-naphtho[2.3-b]pyran-5,10-dione, a pigment of Echinothrix diadema, and its analogs. Natural Product Communications, 10, 1243–1246.
16.
PokhiloND, AtopkinaLN, KiselevaMI, DenisenkoVA, AnufrievVP. (2017) Synthesis and cytotoxic evaluation of glucoconjugated ethylmompain derivatives. Natural Product Communications. 12, 1475–1478.
17.
AnufrievVP, ElyakovGB, PolonikSG, PokhiloND, ShestakOP, YakubovskayaAY, OsadchiySA, TolstikovGA, ShultzEE. (2006) A method of preparation of 5,8-dihydroxy-2,6,7-trimethoxy-3-ethyl-1,4-naphthoquinone. RF Patent No. 2277083, Bulletin Isobreteniy, 15.
18.
BachmannW, StruveW. (1942) in Organic Reactions, Ed. AdamsR., J. Wiley and Sons, New York, p.734.
19.
MooreRE, SinghH, ChangCWJ, ScheuerPJ. (1966) Sodium borohydride reduction of spinochrome A. Removal of phenolic hydroxyls in the naphthazarin system. Journal of Organic Chemistry.31, 3638–3645.
20.
MooreRE, SinghH, ChangCWJ, ScheuerPJ. (1967) Polyhydroxynaphthoquinones. preparation and hydrolysis of methoxyl derivatives. Tetrahedron, 23, 3271–3306.
21.
GlazunovVP, TchizhovaAY, ShestakOP, Sopel'nyakGI, AnufrievVP. (2001) Chemistry of naphtazarin derivatives 8. Determination of structures of substituted 2-hydroxy-6(7)-methoxynaphthazarins and 7(8)-hydroxypyranonaphthazarins by IR spectroscopy. Russian Chemical Bulletin. International Edition, 50, 95–100.