Compound Selection

Formula: C14H19NO4

MW: 265.31

CAS: 22862-76-6

MDL: MFCD06668135

TNP: TNP00269

2-((4-methoxyphenyl)methyl)-,3-acetate,(2r-(2-alpha,3-4-pyrrolidinediol; 2-(p-methoxybenzyl)-,3-acetate,(2s,3r,4r)-4-pyrrolidinediol; 4-beta))-alph; antibioticpa-106; ANISOMYCIN; ANISOMYCIN, STREPTOMYCES GRISEOLUS; FLAGECIDIN; (2R,3S,4S)-2-(4-METHOXYBENZYL)-3,4-

LogP: 0.46

LogS:

Acceptors: 4

Donors: 2

Rotation Bonds: 2

Chiral Centers: 3

N+O: 5

LIPINSKY: 4

IUPAC: (3S,4S)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl acetate

Smiles: COc1ccc(CC2[C@H](OC(=O)C)[C@H](CN2)O)cc1

THERAPEUTIC CATEGORY: Antiprotozoal (Trichomonas)

REFERENCE: Reference Alberts, B., et al., Basic genetic mechanisms in molecular biology of the cell. Cell 3rd ed., New York, NY , 240, (1994) Faris, M., et al., The c-Jun N-terminal kinase cascade plays a role in stress-induced apoptosis in Jurkat cells by up-regulating Fas ligand expression. J. Immunol. 160, 134-144, (1998) abstract Polverino, A.J., Patterson, S.D., Selective activation of caspases during apoptotic induction in HL-60 cells. Effects of a tetrapeptide inhibitor. J. Biol. Chem. 272, 7013, (1997) abstract Zechner, D., et al., MKK6 activates myocardial cell NF-kappaB and inbibits apoptosis in a p38 mitogen-activated protein kinase-dependent manner. J. Biol. Chem. 273, 8232-8239, (1998) abstract Barros, L.F., et al., Evidence of two mechanisms for the activation of the glucose transporter GLUT1 by anisomycin: p38(MAP kinase) activation and protein synthesis inhibition in mammalian cells. J. Physiol. 504, 517-525, (1997) abstract Hoffman, M.E., et al., Inhibition of protein synthesis and amino acid transport by crystal violet in Trypanosoma cruz. J. Eukaryot. Microbiol. 42, 293-297, (1995) abstract Barancik, M., et al., Okadaic acid and anisomycin are protective and stimulate the SAPK/JNK pathway. J. Cardiovasc. Pharmacol. 34, 182-190, (1999) abstract Liao, J., et al., Stress apoptosis and mitosis induce phosphorylation of human keratin 8 at Ser-73 in tissues and cultured cells. J. Biol. Chem. 272, 17565, (1997) abstract Merck Merck 13,673 Beilstein Beil. 21,V,5,523

SOURCE: Antibiotic isolated from Streptomyces griseolus

ACTIVITY: Antibiotic isolated from Streptomyces griseolus that inhibits protein synthesis. Acts by inhibiting peptidyl transferase activity in eukaryote ribosomes. Reported to induce apoptosis in a variety of cells including promyelocytic leukemia cells, Jurkat cells, ventricular myocytes, and colon adenocarcinoma cells. Initiates intracellular signals and immediate early gene induction. Selective signaling agonist. Potent Jun-NH2 terminal kinase (JNK) agonist. Activates mitogen-activated protein (MAP) kinases (JNK/SAPK and p38/RK). Antiprotozoal agent.

Specification: Antibiotics; Protein Kinase ANISOMYCIN Chemical Properties:

mp 140-141 C storage temp. 2-8C solubility methanol: 20 mg/mL, clear, colorless to faintly yellow form solid color white Stability:Stable. Incompatible with strong oxidizing agents. Safety Information Hazard Codes T,Xn Risk Statements 25-36/37/38-20/21/22 Safety Statements 45-36-26 RIDADR UN 3462 6.1/PG 3 WGK Germany 3 RTECS BZ9800000 F 3-10 HazardClass 6.1(b) PackingGroup III ANISOMYCIN Usage And Synthesis Chemical Properties:

Crystalline Biological ActivityProtein synthesis inhibitor (blocks translation). Potent activator of stress-activated protein kinases (JNK/SAPK) and p38 MAP kinase. Acts as a potent signaling agonist to selectively elicit homologous desensitization of immediate early gene induction (c-fos, fosB, c-jun, junB and junD). ANISOMYCIN

Merck 13 Reference: Monograph Number: 0000673

Title: Anisomycin

CAS Registry Number: 22862-76-6

CAS Name: (2R,3S,4S)-2-[(4-Methoxyphenyl)methyl]-3,4-pyrrolidinediol 3-acetate

Additional Names: [2R-(2a,3a,4b)]-2-[(4-methoxyphenyl)methyl]-3,4-pyrrolidinediol 3-acetate; 2-p-methoxyphenylmethyl-3-acetoxy-4-hydroxypyrrolidine; 1,4,5-trideoxy-1,4-imino-5-(4-methoxyphenyl)-D-xylo-pentitol 3-acetate

Trademarks: Flagecidin (Pfizer)

Molecular Formula: C14H19NO4

Molecular Weight: 265.30.

Percent Composition: C 63.38%, H 7.22%, N 5.28%, O 24.12%

Literature References: Protein synthesis inhibiting antibiotic isolated from Streptomyces griseolus and S. roseochromogenes: Sobin, Tanner, Jr., J. Am. Chem. Soc. 76, 4053 (1954); Tanner et al., US 2691618 (1954 to Pfizer). Activity: J. E. Lynch et al., Antibiot. Chemother. 4, 844, 899 (1954). Structure and stereochemistry: Beereboom et al., J. Org. Chem. 30, 2334 (1965); Schaefer, Wheatley, ibid. 33, 166 (1968); Butler, ibid. 2136. Biosynthesis: Butler, ibid. 31, 317 (1966). Total synthesis: Oida, Ohki, Chem. Pharm. Bull. 16, 2086 (1968); ibid. 17, 1405 (1969); Felner, Schenker, Helv. Chim. Acta 53, 754 (1970). Chiral synthesis: J. P. H. Verheyden et al., Pure Appl. Chem. 50, 1363 (1978). Stereospecific total synthesis: D. P. Schumacher, S. S. Hall, J. Am. Chem. Soc. 104, 6076 (1982). Mechanism of action: A. Jim

Chemical Compounds - Natural Compounds

Structure Search Shop Online Download Databases Request a CD
Structure Search eChemStore Download Request CD

Site Search

Compound Search

share

FacebookTwitterLinkedin

Contact Us

Phone: 302-292-8500
Fax: 302-292-8520

MyriaScreen II – diversity screening library from Sigma-Aldrich and TimTec
ApexScreen is a collection of 5,040 compounds that were selected to represent the diversity of TimTec stock
Chemistry reagents, HPLC columns, natural compounds
innovative software packages for chemical database management, chemical web server, structure drawing, diversity analysis, clustering, HTS and combinatorial chemistry, prediction of LogP/solubility/Pk, and Spectra Management