Marvin Carmack

Indiana University Bloomington, Bloomington, IN, United States

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Publications (15)66.67 Total impact

  • Andrew P. Komin · Marvin Carmack
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    ABSTRACT: The o-diamine, 3,4-diamino-1,2,5-thiadiazole (2), was synthesized from 3,4-dichloro-1,2,5-thiadiazole (3) hy three methods. Aqueous glyoxal cyclized 2 into [1,2,5]thiadiazolo[3,4–6]-pyrazine (14). 3,4-Dichloro-1,2,5-thiadiazole 1,1-dioxide (18) reaeted with 2 to give 1,3-dihydro-bis[1,2,5]thiadiazolo[3,4-b:3′,4′-e]pyrazine 2,2-dioxide (19). The reaction of 2 with selenium oxyehloride led to [1,2,5]selenadiazolo[3,4-c] [1,2,5]thiadiazole (12). Ring closure of 2,3-diaminoquinoxaline (4) with thionyl chloride or selenium oxychloride gave [1,2,5]thiadiazolo-[3,4-b]quinoxaline (21) and [1,2,5]selenadiazolo[3,4-b]quinoxaline (22), respectively. Sulfurous acid reduced 21 to the 4,9-dihydro derivative 23, which was reoxidized to 21 with chloranil. Aqueous hase hydrolyzed 21 to 4via the hydrated intermediate 24. Aqueous glyoxal cyclized 4 to the covalent hydrate of pyrazino[2,3-b]quinoxaline (26), 27, which was dehydrated to 26. Compound 26 underwent rapid addition of two alcohols in a process analogous to covalent hydration.
    Journal of Heterocyclic Chemistry 02/1976; 13(1):13 - 22. DOI:10.1002/jhet.5570130102 · 0.79 Impact Factor
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    ABSTRACT: Three extracts of the roots of the plant Lithospermum ruderale (lithosperm) were tested for their ability to inhibit in vivo the action of endogenous and exogenous gonadotropins and of thyrotropin when measured by the 32P uptake of testes and thyroid glands of white Leghorn cockerels. Preparation, BD 893-122, was a crude extract and inhibited both endogenous gonadotropins and thyrotropin in 10-day-old birds. This extract, in addition, produced a 81.5% in vivo inhibition of exogenous TSH in 1-day-old chicks. Fractionation of root extracts on a Sephadex G-50 column resulted in several distinctive polyphenolic fractions, one of which, fraction E, inhibited exogenous FSH and endogenous TSH in 11-day-old cockerels. The inhibition of 32P uptake by the testes demonstrated that 70.8% inhibition of FSH occurred. The E fraction also markedly inhibited endogenous TSH. Fractions from the Sephadex G-50 column were further fractionated on a Sephadex G-25 column and fraction F-3, which was composed of 85% salts of lithospermic acid, was tested in 11-day-old chicks for its inhibitory effect in vivo against exogenous LH and FSH. F-3 inhibited 90.7% of the LH action and 63.5% of the FSH action but it was observed that it did not inhibit endogenous TSH in this experiment. Fractionation on the Sephadex G-25 column appeared to have separated the antigonadotropic and the antithyrotropic activities of lithosperm. The evidence also indicates that LH action was inhibited to a greater degree than was that of FSH.There was no indication that body weights or gland weights were depressed by the lithosperm fractions. It is improbable that the inhibitory action of the lithosperm fractions can be explained on the basis of either toxic effects or of inanition.
    General and Comparative Endocrinology 02/1976; 28(1):24-32. DOI:10.1016/0016-6480(76)90134-9 · 2.47 Impact Factor
  • Charles J. Kelley · Richard C. Harruff · Marvin. Carmack
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    ABSTRACT: The 13C NMR spectra of caffeic acid (3a) and 3-(3,4-dihydroxyphenyl)lactic acid (4a) and a series of their O-alkylated derivatives in neutral aqueous solutions are fully assigned. These chemical shifts are used to assign the carbons of rosmarinic (2) and chlorogenic (5) acids. The foregoing compounds serve as models to interpret the 13C NMR spectrum of lithospermic acid (1), C27H22O12. Also discussed are the 13C NMR spectra of quinic acid (6) and two morphinane derivatives, oxymorphone (10), and oxycodone (11), containing aromatic rings structurally similar to 1.
    The Journal of Organic Chemistry 02/1976; 41(3). DOI:10.1021/jo00865a007 · 4.72 Impact Factor
  • F J Zeller · W R Breneman · M Carmack · C J Kelley
    Biochemical and Biophysical Research Communications 01/1976; 67(3):1234-41. · 2.30 Impact Factor
  • Charles J. Kelley · Marvin Carmack
    Tetrahedron Letters 12/1975; 16(42):3605–3608. DOI:10.1016/S0040-4039(00)91335-2 · 2.38 Impact Factor
  • Frank J. Zeller · W.R. Breneman · Marvin Carmack · C.J. Kelley
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    ABSTRACT: A polyphenolic fraction of the plant was injected into White Leghorn cockerels at various time intervals and the effect on testes and thyroids was measured by the uptake of 32P. The 32P uptake 8 hours after lithosperm2 injection was markedly depressed and 12 hours after administration was notably increased. It is suggested that the hypothalamic regulation of the testes and thyroids is altered by lithosperm interference of the hypothalamic feedback system and/or the binding of receptor sites in the two glands.
    Biochemical and Biophysical Research Communications 12/1975; 67(3):1234-1241. DOI:10.1016/0006-291X(75)90805-0 · 2.30 Impact Factor
  • Andrew P. Komin · Marvin Carmack
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    ABSTRACT: Benzo [1,2-c:3,4-c′:5,6-c″] tris [1,2,5] thiadiazole (1) was synthesized from benzo [1,2-c:3,4-c′] - bis [1,2,5] thiadiazole (11). Nitration of 11 gave compound 15, which on direct amination gave nitroamine 17. Reduction of 17 gave diamine 18, and cyclization of 18 with thionyl chloride gave 1. Diamine 18 was also cyclized with selenium oxychloride, glyoxal, 9,10-phenanthrene-quinone, and formic acid to give the compounds 4, 5, 19, and 6, respectively. A new procedure for the preparation of 2,1,3-benzothiadiazole (7) from o-phenylenediamine was used.
    Journal of Heterocyclic Chemistry 10/1975; 12(5):829-833. DOI:10.1002/jhet.5570120503 · 0.79 Impact Factor
  • Andrew P. Komin · Robert W. Street · Marvin Carmack
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    ABSTRACT: The stable new heteroaromatic compound, [1,2,5]thiadiazolo[3,4-c][1,2,5]thiadiazole (1), was synthesized by three routes. Ring closure of 2 with excess sulfur mono- or dichloride in DMF gave 1. The aminoamidine 9a was isolated from the reaction of 2 with only 1 mol of sulfur dichloride. Diamine 3 could be cyclized to 1 with either thionyl chloride in pyridine or with sulfur monochloride in DMF. Oxamide dioxime (4) closed to 1 when treated with sulfur dichloride in DMF. Hydrolysis of 1 gave 3, which on further hydrolysis gave oxamide.
    The Journal of Organic Chemistry 09/1975; 40(19). DOI:10.1021/jo00907a009 · 4.72 Impact Factor
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    ABSTRACT: The dipotassium salt of 3,4-dihydroxy-1,2,5-thiadiazole 1,1-dioxide (4a) was synthesized in high yield from sulfamide and diethyl oxalate. The free acid (7) was prepared from 4a, from the disilver salt (4c), or from 3,4-dichloro-1,2,5-thiadiazole 1,1-dioxide (13), the latter being synthesized from 4a and phosphorus pentachloride. The reactive 13 was converted in methanol to the dimethoxy derivative (12). Either 12 or 13 reacted with ammonia to form the 3,4-diamino derivative (14) and with methylamine, dimethylamine, and ethylenediamine, respectively, to produce the 3,4-bis(methylamino) (15), the 3,4-bis(dimethylamino) (16), and the 3,4-piperazino (23) derivatives. One mole of morpholine with 12 yielded 3-morpholino-4-methoxy-1,2,5-thiadiazole 1,1-dioxide (17), which could be rearranged smoothly by heating to 2-methyl-3-oxo-4-morpholino-1,2,5-thiadiazoline 1,1-dioxide (18). Two moles of piperidine with 12 gave 3-oxo-4-piperidino-1,2,5-thiadiazoline 1,1-dioxide (19) and N-methylpiperidine. Dimethoxy derivative 12 rearranges thermally, first to 2-methyl-3-oxo-4-methoxy-1,2,5-thiadiazoline 1,1-dioxide (10) and then to 2,5-dimethyl-3,4-dioxo-1,2,5-thiadiazolidine 1,1-dioxide (11). o-Phenylenediamine with 12 in DMF gave the tricyclic 1,3-dihydro[1,2,5]thiadiazolo[3,4-b]quinoxaline 2,2-dioxide (24). 12 and 14 condensed in the presence of sodium methoxide to form a linear tricyclic quinonoid salt (25a). 13 reacted with 2 mol of anthranilic acid to yield a diamine (26) which was dehydrated to a linear pentacyclic bis(quinazolino)-1,2,5-thiadiazole derivative (27).
    The Journal of Organic Chemistry 09/1975; 40(19). DOI:10.1021/jo00907a008 · 4.72 Impact Factor
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    ABSTRACT: A structure is proposed for lithospermic acid (C27H22O12, 1a), the major polyphenolic acid of Lithospermum ruderale and several other plant species of the families, Boraginaceae and Labiatae. Chromatography on Sephadex of aqueous extracts of the plant yields the dipotassium salt of 1a, together with salts of lesser constituents which include (R)-3-(3,4-dihydroxyphenyl)lactic acid (2a), 2-(3,4-dihydroxyphenyl)-3-carboxy-4-(2-carboxy-trans-vinyl)-7-hydroxycoumaran (3a), and rosmarinic acid (4a). Structures were deduced from spectral studies of the salts, the free acids, and also the methylated derivatives produced by the action of diazomethane on the free acids or dimethyl sulfate on the salts.
    The Journal of Organic Chemistry 06/1975; 40(12). DOI:10.1021/jo00900a028 · 4.72 Impact Factor
  • Leonard A. Neubert · Marvin Carmack
    Tetrahedron Letters 12/1974; 15(40):3543–3546. DOI:10.1016/S0040-4039(01)91961-6 · 2.38 Impact Factor
  • Leonard A. Neubert · Marvin Carmack
    Journal of the American Chemical Society 02/1974; 96(3). DOI:10.1021/ja00810a065 · 12.11 Impact Factor
  • Journal of Medicinal Chemistry 07/1972; 15(6):600-3. DOI:10.1021/jm00276a007 · 5.45 Impact Factor
  • Marvin Carmack · Charles J. Kelley
    The Journal of Organic Chemistry 05/1968; 33(5). DOI:10.1021/jo01269a123 · 4.72 Impact Factor
  • Marvin. Carmack · Leonard A. Neubert
    Journal of the American Chemical Society 12/1967; 89(26). DOI:10.1021/ja01002a064 · 12.11 Impact Factor