
Additional Names: C-Toxiferine I
Literature References: Naturally occurring neuromuscular blocker. From calabash curare: Schmid, Karrer, Helv. Chim. Acta 30, 1162 (1947); from Strychnos toxifera Schomb., Loganiaceae: Wieland et al., Ann. 547, 156 (1941); King, J. Chem. Soc. 1949, 3263. Identity with toxiferine V and toxiferine XI: Battersby et al., ibid. 1960, 1848. Structure: Arnold et al., Helv. Chim. Acta 44, 620 (1961). Synthesis: Berlage et al., ibid. 42, 394 (1959); Grdinic et al., J. Am. Chem. Soc. 86, 3357 (1964). Pharmacokinetics: P. G. Waser, J. Reller, Agents Actions 2, 170 (1972). 13C-NMR study: E. Wenkert et al., J. Org. Chem. 43, 1099 (1978).
CAS Name: Cytidine 5'-(trihydrogen diphosphate) P'-[2-(trimethylammonio)ethyl] ester inner salt
Additional Names: choline cytidine 5'-pyrophosphate (ester); cytidine diphosphate choline ester; ...
Literature References: Naturally occurring nucleotide; intermediate in the major pathway of lecithin biosynthesis. Identification: E. P. Kennedy, S. B. Weiss, J. Am. Chem. Soc. 77, 250 (1955). Crystallization from yeast extract: I. Lieberman et al., Science 124, 81 (1956). Synthesis: E. P. Kennedy, J. Biol. Chem. 222, 185 (1956); K. Kikugawa et al., Chem. Pharm. Bull. 19, 1011, 2466 (1971). Molecular structure: M. A. Viswamitra et al., Nature 258, 497 (1975). Series of articles on pharmacology and toxicology: Arzneim.-Forsch. 33, 1009-1080 (1983). Acute toxicity: T. Grau et al., ibid. 1033. Clinical trial in ischemic stroke: W. M. Clark et al., Neurology 49, 671 (1997). Review of biosynthesis, metabolism, pharmacology: G. B. Weiss, Life Sci. 56, 637-660 (1995); and clinical experience: J. J. Secades, G. Frontera, Methods Find. Exp. Clin. Pharmacol. 17, Suppl. B, 1-54 (1995).
CAS Name: [(3S)-3-Amino-3-carboxypropyl]dimethyl sulfonium inner salt
Additional Names: S-methyl-L-methionine; MeMet; vitamin U
Percent Composition: C 44.15%, H 8.03%, N 8.58%, O 19.60%, S 1...
Literature References: Naturally occurring sulfonium compound found in a large number of plants. Identification of antiulcer vitamin in cabbage leaves: G. Cheney, Calif. Med. 77, 248 (1952). Isoln from cabbage juice: R. A. McRorie et al., J. Am. Chem. Soc. 76, 115 (1954). Activity: V. Z. Szabo, G. Vargha, Arzneim.-Forsch. 10, 23 (1960). Determn in plant tissue: P. K. Macnicol, Anal. Biochem. 158, 93 (1986). Review of biosynthesis and physiological role in plants: J. Giovanelli et al., "Sulfur Amino Acids in Plants " in The Biochemistry of Plants 5, B. J. Miflin, Ed. (Academic Press, New York, 1980) pp 453-505.
CAS Name: (3b)-3-Hydroxylup-20(29)-en-28-oic acid
Additional Names: betulic acidPercent Composition: C 78.90%, H 10.59%, O 10.51%
Literature References: Naturally occurring triterpene found in many plant sources, notably the bark of white birch trees, Betula alba L. Betulaceae. Melanoma-specific cytotoxic agent. Isoln: L. Ruzicka et al., Helv. Chim. Acta 21, 1706 (1938); and characterization: A. Robertson et al., J. Chem. Soc. 1939, 1267. Synthesis from betulin, q.v.: D. S. H. Kim et al., Synth. Commun. 27, 1607 (1997). Isoln and crystal structure of benzyl ester: G. Bringmann et al., Planta Med. 63, 255 (1997). Inhibition of HIV replication: T. Fujioka et al., J. Nat. Prod. 57, 243 (1994). Induction of apoptosis in human melanoma cells: E. Pisha et al., Nat. Med. 1, 1046 (1995). Mechanism of action study: S. Fulda et al., Cancer Res. 57, 4956 (1997). Pharmacokinetics in mice: G. O. Udeani et al., Biopharm. Drug Dispos. 20, 379 (1999). Tumor cell-specific cytotoxicity: V. Zuco et al., Cancer Lett. 175, 17 (2002). LC/MS determn in plasma: X. Cheng et al., Rapid Commun. Mass Spectrom. 17, 2089 (2003). Review of natural distribution: G. Pavanasasivam, M. U. S. Sultanbawa, Phytochemistry 13, 2002-2006 (1974); of anticancer activity: D. A. Eiznhamer, Z.-Q. Xu, IDrugs 7, 359-373 (2004); of chemistry, biology and therapeutic potential: R. H. Cichewicz, S. A. Kouzi, Med. Res. Rev. 24, 90-114 (2004); of biological properties: P. Yogeeswari, D. Sriram, Curr. Med. Chem. 12, 657-666 (2005).
CAS Name: 13-cis-Retinol
Additional Names: 2-cis-vitamin A
Percent Composition: C 83.86%, H 10.56%, O 5.59%
Literature References: Naturally occurring, bioactive isomer of vitamin A, q.v. The 13-cis- and all-trans-forms come to equilibrium in solution with ~33% as 13-cis. Isoln from shark liver oil: C. D. Robeson, J. G. Baxter, J. Am. Chem. Soc. 69, 136 (1947). Synthesis: M. Matsui et al., J. Vitaminol. 4, 178 (1958). Stereoselective synthesis: J. Otera et al., Chem. Lett. 1985, 1883. HPLC determn in food samples: E. Brinkmann et al., J. Chromatogr. A 693, 271 (1995). Review of vitamin A compounds: W. Friedrich in Vitamins (Walter de Gruyter, Berlin, 1988) pp 63-140.
CAS Name: N6-[(3R)-1,5-Didehydro-3-methyl-D-prolyl]-L-lysine
Additional Names: L-pyrrolysine
Percent Composition: C 56.45%, H 8.29%, N 16.46%, O 18.80%
Literature References: Naturally occurring, genetically encoded amino acid found in certain methanogenic Archaea; originally described as L-lysine e-amide linked to (4R,5R)-4-substituted-1-pyrroline-5-carboxylate. Identification of pyrrolysine-specific tRNA in Methanosarcina barkeri: G. Srinivasan et al., Science 296, 1459 (2002). Identification as UAG-encoded residue in monomethylamine methyltransferase: B. Hao et al., ibid. 1462. Identification of C4-substituent as a methyl group, synthesis and properties: idem et al., Chem Biol. 11, 1317 (2004). MS analysis: J. A. Soares et al., J. Biol. Chem. 280, 36962 (2005). Reviews: C. Fenske et al., Angew. Chem. Int. Ed. 42, 606-610 (2003); J. A. Krzycki, Curr. Opin. Microbiol. 8, 706-712 (2005).
CAS Name: (7S)-6,7-Dihydro-7-[[(2S,9S,9aS)-2,3,9,9a-tetrahydro-9-hydroxy-2-(2-methylpropyl)-3-oxo-1H-imidazo[1,2-a]indol-9-yl]methyl]quinazolino[3,2-a][1,4]benzodiazepine-5,13-dione
Percent Com...
Literature References: Naturally occurring, nonpeptide cholecystokinin (CCK) antagonist. Produced by several strains of Aspergillus alliaceus along with minor related compounds known as asperlicin B, C, D and E. Isoln from fermentation cultures of A. alliaceus Thom and Church, ATCC 20655 and ATCC 20656: R. L. Monaghan et al., EP 116150; eidem, US 4530790 (1984, 1985 both to Merck Co.). Fermentation, isoln and bioactivity: M. A. Goetz et al., J. Antibiot. 38, 1633 (1985); of asperlicins B, C, D and E: eidem, ibid. 41, 875 (1988). Structure elucidation: J. M. Liesch et al., ibid. 38, 1638 (1985); of asperlicins B, C, D and E: eidem, ibid. 41, 878 (1988). Biosynthetic study: D. R. Houck et al., ibid. 882. Total synthesis of asperlicins C and E: M. G. Bock et al., J. Org. Chem. 52, 1644 (1987). Pharmacology of asperlicin: R. S. L. Chang et al., Science 230, 177 (1985). Effect on pancreatic enzyme secretion in vitro: K. A. Zucker et al., Surgery 102, 163 (1987). Effect in exptl pancreatitis in rats: J. R. Wisner, Jr., I. G. Renner, Pancreas 3, 174 (1988).
CAS Name: Methylphosphonothioic acid S-[2-[bis(1-methylethyl)amino]ethyl] O-ethyl ester
Additional Names: O-ethyl S-[2-(diisopropylamino)ethyl]methylphosphonothioate; Tx 60
Percent Compositi...
Literature References: Nerve gas. Prepn: R. V. Ley, G. L. Sainsbury, GB 1346409; A. W. Wardrop, C. Stratford, GB 1346410 (both 1974 to U.K. Sec. of State for Defence), C.A. 81, 4068y, 4069z (1974); S. R. Eckhaus et al., US 3911059 (1975 to U.S.A. Sec. for Army). Activity studies in humans: F. R. Sidell, W. A. Groff, Toxicol. Appl. Pharmacol. 27, 241 (1974); F. N. Craig et al., J. Invest. Dermatol. 68, 357 (1977). Toxicity study: J. J. Gordon, L. Leadbeater, Toxicol. Appl. Pharmacol. 40, 109 (1977).
CAS Name: Dimethylphosphoramidocyanidic acid, ethyl ester
Additional Names: ethyl N-dimethylphosphoramidocyanidate; dimethylamidoethoxyphosphoryl cyanide; GA
Percent Composition: C 37.04%, H...
Literature References: Nerve gas; potent cholinesterase inhibitor similar in structure and activity to sarin and soman, q.q.v. Prepd from dimethylamidophosphoryl dichloride and sodium cyanide in the presence of ethanol: Holmstedt, Acta Physiol. Scand. 25, Suppl. 90, 26 (1951). Synthesis of dimethylamidophosphoryl dichloride: Michaelis, Ann. 326, 129 (1903). Alternate synthetic route: B. C. Saunders, Some Aspects of the Chemistry and Toxic Action of Organic Compounds Containing Phosphorus and Fluorine (Cambridge, 1957) p 91. Toxicity study: B. Holmstedt, Pharmacol. Rev. 11, 567 (1959). Brief review: Schrader, Die Entwicklung neuer insektizider Phosphorsäure-Ester (Verlag Chemie, Weinheim, 1963) p 3; B. L. Harris in Kirk-Othmer Encyclopedia of Chemical Technology vol. 5 (Wiley-Interscience, New York, 4th ed., 1993) pp 795-816.
CAS Name: Methylphosphonofluoridic acid 1,2,2-trimethylpropyl ester
Additional Names: pinacoloxymethylphosphoryl fluoride; pinacolyl methylphosphonofluoridate; GD
Percent Composition: C 46.1...
Literature References: Nerve gas; potent cholinesterase inhibitor similar in structure and activity to sarin and tabun, q.q.v. Prepn: Holmstedt, Acta Physiol. Scand. 25, suppl. 90, p 106 (1951); Protar 16, 131 (1950); G. Schrader, Die Entwicklung neuer Insektizide auf Grundlage organischer Fluor- und Phosphor-Verbindungen [Monographie Nr. 62 zu Angewandte Chemie und Chemie-Ingenieur-Technik (Verlag Chemie 1951)]; B. C. Saunders, Some Aspects of the Chemistry and Toxic Action of Organic Compounds Containing Phosphorus and Fluorine (Cambridge, 1957) p 94. Toxicity study: Loomis, Salafsky, Toxicol. Appl. Pharmacol. 5, 685 (1963). Brief description: B. L. Harris in Kirk-Othmer Encyclopedia of Chemical Technology vol. 5 (Wiley-Interscience, New York, 4th ed., 1993) pp 795-816.
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