
Additional Names: Streptovarycin
Literature References: A complex of ansamycin antibiotics consisting of streptovaricins A, B, C, D, E, F, G, J and K of which streptovaricin C is the major component. Isolation from Streptomyces spectabilis: Siminoff et al., Am. Rev. Tuberc. Pulm. Dis. 75, 576 (1957); Whitfield et al., ibid. 584; and resolution of components: Dietz et al., US 3116202 (1963 to Upjohn). Characterization of complex: Rinehart et al., Chem. Commun. 1974, 861. Preliminary structural studies: Rinehart et al., J. Am. Chem. Soc. 88, 3149, 3150 (1966); 90, 6241 (1968); Rinehart et al., ibid. 93, 6273 (1971). Revised structure of streptovaricin C: Sasaki et al., J. Antibiot. 25 68 (1972); Rinehart, Antosz, ibid. 71. Activity studies: Quintrell, McAuslan, J. Virol. 6, 485 (1970); Tan, McAuslan, Biochem. Biophys. Res. Commun. 42, 230 (1971); Carter et al., Nature New Biol. 232, 212, 214 (1971). Biosynthetic study: P. V. Deshmukh et al., J. Am. Chem. Soc. 98, 870 (1976). 13C-NMR studies: K. B. Kakinuma et al., J. Org. Chem. 41, 1358 (1976). Synthesis of a key intermediate for the total synthesis of streptovaricin A: P. A. McCarthy, Tetrahedron Lett. 23, 4199 (1982). Synthesis of the naphthalene core of streptovaricin D: B. M. Trost, W. H. Pearson, ibid. 24, 269 (1983). Review of the chemistry of streptovaricins: K. L. Rinehart et al., Fortschr. Chem. Org. Naturst. 33, 231-307 (1976).
CAS Name: (1R)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one
Additional Names: (1R,5R)-(+)-2-pinen-4-one
Percent Composition: C 79.95%, H 9.39%, O 10.65%
Literature References: A constituent of Spanish verbena oil (from Verbena triphylla L., Verbenaceae): Kerschbaum, Ber. 33, 885 (1900). Prepn from a-pinene: Bain, Gary, US 2911442 (1959 to Glidden). Structure: Blumann, Zeitschel, Ber. 46, 1178 (1913); Weinhaus, Schumm, Ann. 439, 20 (1924). Absolute configuration: Hurst, Whitham, J. Chem. Soc. 1960, 2864. Review: J. L. Simonsen, The Terpenes vol. II (University Press, Cambridge, 2nd ed., 1949) p 232-239.
CAS Name: 2,7,7-Trimethylbicyclo[3.1.1]heptan-6-one
Additional Names: 2-pinen-7-one
Percent Composition: C 79.95%, H 9.39%, O 10.65%
Literature References: A constituent of the essential oil of Chrysanthemum indicium L., also extracted from C. sinense Sabin, Compositae. Prepared by photochemical rearrangement of l- or d-verbenone, q.v.: Hurst, Whitham, J. Chem. Soc. 1960, 2864; Erman, J. Am. Chem. Soc. 89, 3828 (1967); Schuster, Widman, Tetrahedron Lett. 1971, 3571. Structure: Kotake, Nonaka, Ann. 607, 153 (1957); Blanchard, Chem. Ind. (London) 1958, 293. Chemistry: Erman, J. Am. Chem. Soc. 91, 779 (1969).
Additional Names: b-Angiotensin I converting enzyme (formerly)
Literature References: A converting enzyme that differs from renin, q.v., in its ability to form angiotensin II directly from angiotensinogen by cleaving the Phe-His bond; it can also convert angiotensin I to angiotensin II. Its presence was discovered in rat submaxillary glands: R. Boucher et al., Hypertension 72, J. Genest, E. Koiw, Eds. (Springer-Verlag, New York, 1972) p 512; eidem, Circ. Res. Suppl. I, 203 (1974). Purification and characterization: S. Demassieux et al., Can. J. Biochem. 54, 788 (1976). Crystal data: K. Hayakawa et al., J. Mol. Biol. 123, 107 (1978). Radioimmunoassay: J. Gutkowska et al., Can. J. Biochem. 56, 769 (1978). Purification by affinity chromatography: M. Ikeda et al., Hypertension 3, 81 (1981); by gel permeation and HPLC: C. Lazure et al., Anal. Biochem. 125, 406 (1982). Isoln using chromatofocusing: E. S. P. Cheng, B. J. Morris, ibid. 126, 295 (1982). N-Terminal amino acid sequence of rat tonin: N. G. Seidah et al., Can. J. Biochem. 56, 920 (1978). Substrate specificity studies: eidem, Proc. Am. Peptide Symp. 6th, E. Gross, J. Meienhofer, Eds. (Pierce Chem. Co., Rockford, Ill., 1979) p 921; M. Chretien et al., FEBS Lett. 113, 173 (1980). Formation of angiotensin II by tonin from partially purified human angiotensinogen: C. Grise et al., Can. J. Biochem. 59, 250 (1981). Pressor effect in anephric animals: E. L. Schiffrin et al., Can. J. Physiol. Pharmacol. 59, 864 (1981). Sequence homologies between tonin and other peptides: C. Lazure et al., Nature 292, 383 (1981). Immunohistochemical study: T. B. Oerstavik et al., J. Histochem. Cytochem. 30, 1123 (1982). Role as renin activator: J. Gutkowska et al., Can. J. Biochem. 60, 843 (1982). Role in exptl hypertension: R. Garcia et al., Hypertension, Int. Symp., 3rd, H. Villarreal, Ed. (Wiley, New York, 1981) p 79. Reviews: R. Boucher et al., Circ. Res. Suppl. II, 26-29 (1977); R. Boucher, J. Genest, Endocrine Functions of the Brain, M. Motta, Ed. (Raven Press, New York, 1980) pp 373-384; J. Genest, Heterogeneity of Renin and Renin Substrate, M. P. Sambhi, Ed. (Elsevier, New York, 1981) pp 11-24.
CAS Name: [2R-(2a,3b,3ab,9ab)]-2,3,3a,9a-Tetrahydro-3-hydroxy-6-imino-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidine-2-methanol
Additional Names: 2,2'-anhydro-(1b-D-arabinofuranosyl)cytosine; 2,2'-...
Literature References: A cytostatic agent and intermediate in the synthesis of cytarabine, q.v. Prepn of the hydrochloride: E. R. Walwick et al., Proc. Chem. Soc. London 1959, 84; T. Y. Shen, W. V. Ruyle, US 3463850 (1969 to Merck Co.); E. K. Hamamura et al., J. Med. Chem. 19, 654 (1976). General pharmacological properties: H. Hirayama et al., Oyo Yakuri 6, 1259 (1972), C.A. 79, 49175f (1973). Metabolism: D. H. W. Ho, Drug Metab. Dispos. 1, 752 (1973). Biochemical study: idem, Biochem. Pharmacol. 23, 1235 (1974). Pharmacokinetic study: H. S. Chen, J. F. Gross, Cancer Chemother. Pharmacol. 2, 85 (1979). Clinical studies: J. Z. Finklestein et al., Cancer Treat. Rep. 63, 1331 (1979); T. Miale et al., ibid. 1913. Toxicity studies: K. Sugihara et al., Oyo Yakuri 8, 1469 (1974); H. Hirayama et al., ibid. 1693, C.A. 83, 71766, 37747 (1975). HPLC study: V. Reichelova et al., J. Chromatogr. 588, 147 (1991).
CAS Name: 4,5,7,8,9,12-Hexahydro-11H-pyrano[3,4-d]pyrrolo[3,2,1-jk][1]benzazepin-11-one
Percent Composition: C 74.67%, H 6.27%, N 5.80%, O 13.26%
Literature References: A degradation product of b-erythroidine. Prepd by heating b-erythroidine to 120° with phosphoric or sulfuric acid: Sauvage et al., Science 109, 627 (1947); by reacting b-erythroidine with concd hydrobromic acid at 100°: Koniuszy, Folkers, J. Am. Chem. Soc. 73, 333 (1951). Synthesis and structure: Blake et al., J. Am. Chem. Soc. 87, 1397 (1965).
CAS Name: Dihydro-3-hydroxy-4H-dimethyl-2(3H)-furanone
Additional Names: pantoic acid g-lactone; pantoyl lactone; pantoic lactone; 2,4-dihydroxy-3,3-dimethylbutyric acid g-lactone; a-hydroxy-b,...
Literature References: A degradation product of pantothenic acid from liver: Williams, Major, Science 91, 246 (1940). Important intermediate in the synthesis of pantothenic acid. May be prepd by condensing isobutyraldehyde with formaldehyde yielding a,a-dimethyl-b-hydroxypropionaldehyde which is condensed with hydrocyanic acid in the presence of calcium chloride to form racemic pantolactone. Various modifications of this procedure exist: Glaser, Monatsh. Chem. 25, 46 (1904); Stiller et al., J. Am. Chem. Soc. 62, 1785 (1940); Reichstein, Grüssner, Helv. Chim. Acta 23, 650 (1940); Carter, Ney, J. Am. Chem. Soc. 63, 312 (1941). Vast patent literature, e.g., Beckmann et al.; Klein, US 2967869 and US 3024250 (1961, 1962, both to Nopco).
CAS Name: (5'a,6'a)-7,7',8,8'-Tetradehydro-4,5:4',5'-diepoxy-17,17'-dimethyl-[2,2'-bimorphinan]-3,3',6,6'-tetrol
Additional Names: 2,2'-bimorphine; pseudomorphine (C34 alkaloid)
Percent Comp...
Literature References: A dimolecular base formed by the gentle oxidation of morphine in alkaline soln. Refs: Broockmann, Polstorff, Ber. 13, 88 (1880); Bentley, Dyke, J. Chem. Soc. 1959, 2574. Review and bibliography: K. W. Bentley, The Chemistry of the Morphine Alkaloids (Oxford, 1954) p 54.
CAS Name: Nitrilotriacetic acid bismuth complex sodium salt
Trademarks: Bistrimate (SM P)
Percent Composition: C 25.23%, H 2.47%, Bi 18.29%, N 4.90%, Na 14.09%, O 35.01%
Literature References: A double salt of sodium bismuthyl triglycollamate and disodium triglycollamate. Prepn: Lehman, Sproull, US 2348984 (1944).
Additional Names: Antibiotic B-41
Literature References: A family of novel macrolide antibiotics with insecticidal and acaricidal activity; structurally related to avermectin, q.v., aglycones. Isoln from Streptomyces hygroscopicus subsp. aureolacrimosus and properties: A. Aoki et al., DE 2329486; eidem, US 3950360 (1973, 1976 both to Sankyo); of a1-a10, b1-b3, D-H: Y. Takiguchi et al., J. Antibiot. 33, 1120 (1980). Isoln and properties of D-H: Y. Takiguchi et al., J. Antibiot. 36, 502 (1983); of J and K: M. Ono et al., ibid. 509. Structures of milbemycins a1-a10, b1: M. Kurabayashi et al., 18th Symp. Chem. Natural Products (Kyoto, 1974) nos. 309-316; of b1-b3: H. Mishima et al., Tetrahedron Lett. 1975, 711; of D-H, J, K: H. Mishima et al., J. Antibiot. 36, 980 (1983). Total synthesis of (±)-milbemycin b3: A. B. Smith et al., J. Am. Chem. Soc. 104, 4015 (1982); of the (+)-form: D. R. Williams et al., ibid. 4708. Prepn of milbemycins from avermectins: H. Mrozik et al., Tetrahedron Lett. 1983, 5333. Total synthesis studies of D: M. T. Crimmins et al., ibid. 28, 3651 (1987). Prophylactic use of milbemycin D against Dirofilaria immitis infection in dogs: M. Tagawa et al., Jpn. J. Vet. Sci. 47, 787 (1985). Toxicity data: N. Matsunuma et al., Sankyo Kenkyusho Nempo 35, 71 (1983), C.A. 101, 32870d (1984). Review of syntheses: T. Blizzard et al., in Recent Prog. Chem. Synth. Antibiotics, G. Lukacs, M. Ohno, Eds (Springer-Verlag, Berlin, 1990) pp 66-102. Review of structure-activity relationships: W. L. Shoop et al., Vet. Parasitol. 59, 139-156 (1995).
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