1985
DOI: 10.1002/anie.198505011
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A Nucleolipid with Antiviral Acycloguanosine as Head Group—Synthesis and Liposome Formation

Abstract: LiGe, the G e partial structure consists of a three-dimensional network of tricoordinated germanium atoms. However, the electric conductivity now shows metallic behavior. In LiSn and LiPb, no tricoordinated arrangement of the Sn and Pb atoms, respectively, is found. The Sn atoms still have four Sn neighbors in LiSn; the Pb atoms in LiPb have even six Pb neighbors. In this case, metallic phases are present.

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Cited by 15 publications
(5 citation statements)
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“…Few examples in the literature report the direct functionalization of heterocycles' nucleobases with a lipid moiety. Purine's N9 and pyrimidine's N1, chemically bound to the sugar moiety in nucleosides and nucleotides, are possible reactive positions for the attachment of a lipid chain, an example 45 is the synthesis of an acycloguanosine (Acyclovir) lipid derivative with therapeutic properties for the treatment of Herpes simplex (Type I). An acylguanosine nucleolipid, effective in the treatment of the same disease, has been reported by Welch and co-workers.…”
Section: Purinic or Pyrimidinic Heterocycle Functionalizationmentioning
confidence: 99%
“…Few examples in the literature report the direct functionalization of heterocycles' nucleobases with a lipid moiety. Purine's N9 and pyrimidine's N1, chemically bound to the sugar moiety in nucleosides and nucleotides, are possible reactive positions for the attachment of a lipid chain, an example 45 is the synthesis of an acycloguanosine (Acyclovir) lipid derivative with therapeutic properties for the treatment of Herpes simplex (Type I). An acylguanosine nucleolipid, effective in the treatment of the same disease, has been reported by Welch and co-workers.…”
Section: Purinic or Pyrimidinic Heterocycle Functionalizationmentioning
confidence: 99%
“…Bond angle [8] 2a 2b C(2)ÀN(1)ÀC(7a) 112.8(1) 112.8(2) N(1)ÀC(2)ÀN (3) 127.9(1) 126.6(2) C(4)ÀN(3)ÀC (2) 116.4(1) 116.8(2) N(3)ÀC(4)ÀC(4a) 123.5(2) 124.1(2) N(3)ÀC(4)ÀCl (4) 116.5(1) 116.0(2) C(4a)ÀC(4)ÀCl (4) 120.0(1) 120.0(2) C(4)ÀC(4a)ÀC(7a) 113.5(1) 113.4(2) C(4)ÀC(4a)ÀC (5) 139.0(2) 139.2(2) C(7a)ÀC(4a)ÀC (5) 107.5(1) 107.4(2) C(6)ÀC(5)ÀC(4a) 105.6(1) 106.3(2) C(5)ÀC(6)ÀN (7) 111.4(1) 110.4(2) C(7a)ÀN(7)ÀC (6) 107.4(1) 108.1(2) C(7a)ÀN(7)ÀC (8) 126.8(1) 126.0(2) C(6)ÀN(7)ÀC (8) 125.5(1) 125.7(2) N(1)ÀC(7a)ÀN (7) 126.0(1) 125.8(2) N(1)ÀC(7a)ÀC(4a) 125.9(1) 126.3(2) N(7)ÀC(7a)ÀC(4a) 108.1(1) 107.9(2) N(7)ÀC(8)ÀC (9) 111.0(1) 113.2(2) C(8)ÀC(9)ÀBr (1) 108.2(1) 111.5(2) Torsion angle [8] 2a 2b C(7a)ÀN(7)ÀC(8)ÀC(9) À 59.4(2) À 126.5(2) C(6)ÀN(7)ÀC(8)ÀC (9) 128.6(2) 59.6(3) N(7)ÀC(8)ÀC(9)ÀBr(1) À 175.7(1) 60.9 (2) The second fraction contained the title compound 2a. The product-containing fractions were pooled, and the solvent was evaporated.…”
Section: Experimental Partmentioning
confidence: 99%
“…Carboxyalkyl-functionalized derivatives of 7-deazapurines are of interest because they can be easily coupled to polymers or surfaces carrying amino functions lending them the functionality of a particular modified nucleobase [6]. Coupling of such compounds to amino-functionalized lipids or phospholipids [7][8][9] such as kephalines may lead to potential organo-or hydrogelators. It has been shown that for the successful preparation of a gelator, a control of the balance between the hydrophilicity and hydrophobicity of the heterocyclic head group and the lipid tail is of decisive importance [10].…”
Section: M590 (Page 2)mentioning
confidence: 99%