Synthesis of 3-hydroxy-19-nor[21-14C]pregna-1,3,5(10)-trien-20-one from [14C]methyl iodide

Schulster, Dennis; Whitehead, JK; Kellie, A. E.

doi:10.1042/bj0930512

Cited by 6 publications

(1 citation statement)

References 8 publications

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“…The combined organic solution was washed (ice-cold water and brine), dried (MgS04), and evaporated to dryness. Crystallization from benzene-hexane gave (2-chloroethyl)carbamoyl azide as a colorless crystalline product (15 (C=0), 2150, 2170 (N3), 3420 cm"1 (NH); NMR 3.62 (m, unresolved, 4 H, C1CH2CH2N-), 5.93 (br s, 1 , NH).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of steroidal nitrosoureas with antitumor activity

Lam¹,

Begleiter²,

Goldenberg³

et al. 1979

J. Med. Chem.

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Section: Methodsmentioning

confidence: 99%

Synthesis of steroidal nitrosoureas with antitumor activity

Lam¹,

Begleiter²,

Goldenberg³

et al. 1979

J. Med. Chem.

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Synthesis of oxochlorins from the red blood pigment heme and their transformation into potentially biologically active chlorin derivatives

Bats¹,

Haake²,

Meier³

et al. 1995

Liebigs Ann./Recl.

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The hydroxychlorin rac-3 was prepared from the readily accessible chlorins rac-Sa, b. The alcohol function of rac-3 could be used to attach an estrogen residue 28 and the hydroquinone 19 to yield the chlorin estrogen ethers 32a, b and the chlorin hydroquinone ether rac-30 respectively. The prepared chlorin estrogen derivatives might be useful as sensitiChlorophyll a, the green pigment of plant photosynthesis, is the prototype of the chlorin class of natural products[*] which today includes a number of compounds with differing structures and functions. The common structural unit in this class is the chlorin framework 1 with a partially saturated pyrrole ring, which arises from the completely unsaturated porphyrin. On account of their photophysical properties the chlorins resulting from this structural modifications are suitable for use as pigments in photosynthesi~ [~] and for medical applications, for example in photodynamic tumor therapy (PDT)r41.We have recently shown that chlorins like rac-2a, ruc-2b, and rac-4 can easily be derived from the red blood pigment hemeus]. In this paper we describe the further functionalization of chlorin ruc-2a by degradation of the exocyclic double bond in the 3-position. The functional group may be used to attach different residues. Artificial photosynthesis systems may thus be prepared containing "natural" chlorins as the structural units in contrast to the previously synthesized model systems based on porphyrins. The functionalized chlorin rac-3 may also be modified to provide sensitizer structures and fluorescence marked6] for photodynamic tumor therapy and other therapeuticldiagnostic applications. Synthesis of Oxochlorins and Their Further TransformationThe chlorin structure ruc-4 bearing a lipophilic heptyl side chain was recently prepared in our laboratory with respect to an application in PDT, because amphiphilic properties of sensitizers might be decisive for biological activity. The liphophilic side chain had to be introduced into the macrocycle at the very beginning of the synthesis, so that each of other possible active structures would require its individual preparative pathway. Therefore, we aimed at the synthesis of the oxochlorins mc-9 and rac-10 and the ~~~~~~~ zers and fluorescence markers for photodynamic therapy and other diagnostichherapeutic applications. The chlorin hydroquinone ether is of interest as a potential artificial photosynthesis system, which contains a "natural" chlorin as a structural subunit in contrast to previously synthesized model systems based on porphyrins.hydroxychlorin ruc-3 which have functional groups to which different residues can be attached to alter properties. Since it was expected that the chlorin chromophore could be sensitive to the oxidation conditions required for the cleavage of the exocyclic double bond we first transformed the more stable known nickelchlorin racda. b[5b1 into the

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