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AT 2433 A2

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AT 2433 A2
Category Antibiotics
Catalog number BBF-03213
CAS 102644-19-9
Molecular Weight 665.09
Molecular Formula C33H33ClN4O9
Purity >98%

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

AT 2433 A2 is an anti-tumor antibiotic produced by Actinomadura melliaura. It has activity against gram-positive bacteria.

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Synonyms AT 2433-A2; AT2433-A2
Storage Store at -20°C
IUPAC Name 3-[(2R,3R,4R,5S,6R)-6-[[(2S,4S,5S)-5-amino-4-hydroxyoxan-2-yl]oxymethyl]-3,4-dihydroxy-5-methoxyoxan-2-yl]-5-chloro-13-methyl-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17,19,21-nonaene-12,14-dione
Canonical SMILES CN1C(=O)C2=C3C4=C(C(=CC=C4)Cl)N(C3=C5C(=C2C1=O)C6=CC=CC=C6N5)C7C(C(C(C(O7)COC8CC(C(CO8)N)O)OC)O)O
InChI InChI=1S/C33H33ClN4O9/c1-37-31(42)23-21-13-6-3-4-9-17(13)36-25(21)27-22(24(23)32(37)43)14-7-5-8-15(34)26(14)38(27)33-29(41)28(40)30(44-2)19(47-33)12-46-20-10-18(39)16(35)11-45-20/h3-9,16,18-20,28-30,33,36,39-41H,10-12,35H2,1-2H3/t16-,18-,19+,20-,28+,29+,30+,33+/m0/s1
InChI Key GZGADZPEYFVGGH-NWPISFAASA-N
Antibiotic Activity Spectrum Gram-positive bacteria; Neoplastics (Tumor)
Boiling Point 911.5±65.0°C at 760 mmHg
Density 1.8±0.1 g/cm3
Solubility Soluble in DMSO
1. AT2433-A1, AT2433-A2, AT2433-B1 and AT2433-B2 novel antitumor compounds produced by Actinomadura melliaura. II. Structure determination
J Golik, T W Doyle, B Krishnan, G Dubay, J A Matson J Antibiot (Tokyo). 1989 Dec;42(12):1784-9. doi: 10.7164/antibiotics.42.1784.
The chemical structures of AT2433-A1 (2), AT2433-A2 (3), AT2433-B1 (4) and AT2433-B2 (5) were elucidated by degradation and spectroscopic studies. Compounds 2-5 are disaccharides closely related to rebeccamycin. The aglycone in 2 and 3 was determined to be 6-N-methyl-11-chloro-5H-indolo[2,3-a]pyrolo[3,4-c]carbazole and in 4 and 5 it was determined to be 6-N-methyl-5H-indolo[2,3-a]pyrolo[3,4-c]carbazole. Compounds 2 and 4 are 4-N"-methyl analogs of 3 and 5.
2. AT2433-A1, AT2433-A2, AT2433-B1, and AT2433-B2 novel antitumor antibiotic compounds produced by Actinomadura melliaura. Taxonomy, fermentation, isolation and biological properties
J A Matson, C Claridge, J A Bush, J Titus, W T Bradner, T W Doyle, A C Horan, M Patel J Antibiot (Tokyo). 1989 Nov;42(11):1547-55. doi: 10.7164/antibiotics.42.1547.
Compounds AT2433-A1 (A1), AT2433-A2 (A2), AT2433-B1 (B1), and AT2433-B2 (B2) were isolated from the cultured broth of Actinomadura melliaura sp. nov. (SCC 1655). Structurally these materials are closely related to rebeccamycin (1), an indolocarbazole antitumor antibiotic. A1, A2, B1, and B2 were active against Staphylococcus aureus A9537, Streptococcus faecalis A20688, Streptococcus faecium (ATCC 9790), Micrococcus lutea (ATCC 9341), Bacillus subtilis (ATCC 6633). A1 and B1 were active against P388 leukemia in mice.

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