Sangivamycin hydrochloride
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| Category | Antibiotics |
| Catalog number | BBF-02862 |
| CAS | 21090-35-7 |
| Molecular Weight | 345.74 |
| Molecular Formula | C12H15N5O5.HCl |
| Purity | 95% |
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Description
Sangivamycin hydrochloride is a nucleoside (purine) antibiotic produced by the strain of Str. rimosus BA-90912. 0.02-0.05 μg/mL of Sangivamycin inhibits HeLa cells. It has weak inhibitory effect on sarcoma-180 and adenocarcinoma 755 in mice. It has obvious inhibitory effect on leukemia L-1210. When intraperitoneally administered, the drug binds to nucleic acids in tissues in mice through phosphorylation.
Specification
| Related CAS | 18417-89-5 (free base) |
| Synonyms | Sangivamycin monohydrochloride; 7H-Pyrrolo(2,3-d)pyrimidine-5-carboxamide, 4-amino-7-beta-D-ribofuranosyl-, monohydrochloride; 7-Deazaadenosine-7-carboxamide hydrochloride |
| Storage | Store at 2-8°C under inert atmosphere |
| IUPAC Name | 4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carboxamide;hydrochloride |
| Canonical SMILES | C1=C(C2=C(N=CN=C2N1C3C(C(C(O3)CO)O)O)N)C(=O)N.Cl |
| InChI | InChI=1S/C12H15N5O5.ClH/c13-9-6-4(10(14)21)1-17(11(6)16-3-15-9)12-8(20)7(19)5(2-18)22-12;/h1,3,5,7-8,12,18-20H,2H2,(H2,14,21)(H2,13,15,16);1H/t5-,7-,8-,12-;/m1./s1 |
| InChI Key | WTSGTUMQZSEZIW-CCUUNMJDSA-N |
Properties
| Appearance | Colorless Long Needle Crystal |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 810.4°C at 760 mmHg |
| Melting Point | 254-255°C |
| Solubility | Soluble in Methanol |
Reference Reading
1. Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin
N Nishimura, A Kato, I Maeba Carbohydr Res. 2001 Mar 9;331(1):77-82. doi: 10.1016/s0008-6215(01)00017-9.
Syntheses of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides are reported. Treatment of pyranulose glycoside with aminoguanidine in acetic acid gave the corresponding semicarbazone in 96% yield. The ring transformation of the semicarbazone in dioxane afforded a 51% yield of 2-amino-7-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)pyrrolo[2,1-f]-[1,2,4]triazine. Vilsmeier formylation of the pyrrolotriazine gave the major product, 5-formylpyrrolo[2,1-f][1,2,4]triazine, in 69% yield. The aldehyde was treated with hydroxylamine hydrochloride in methanol to give aldoximes. Dehydration of aldoxime with trifluoromethanesulfonic anhydride and triethylamine in dichloromethane afforded 5-cyanopyrrolo[2,1-f][1,2,4]triazine in 44% yield. Conversion of the nitrile to the deprotected amide, 2-amino-7-(beta-D-ribofuranosyl)pyrrolo[2,1-f][1,2,4]triazine-5-carboxamide, was accomplished in 96% yield on treatment with 30% H2O2 in ethanol for 1 day at room temperature. Debenzoylation with sodium hydroxide solution produced deprotected C-nucleosides.
2. Nucleic acid related compounds. 51. Synthesis and biological properties of sugar-modified analogues of the nucleoside antibiotics tubercidin, toyocamycin, sangivamycin, and formycin
E De Clercq, J Balzarini, D Madej, F Hansske, M J Robins J Med Chem. 1987 Mar;30(3):481-6. doi: 10.1021/jm00386a007.
Treatment of 7-amino-3-beta-D-ribofuranosylpyrazolo[4,3-d]pyrimidine (formycin) with alpha-acetoxyisobutyryl bromide followed by deprotection of the resulting trans-vicinal acetoxy bromides and hydrogenolysis of the separated bromohydrins gave 2'-deoxy-(23%) and 3'-deoxyformycin (32%) after complete deprotection and purification of their hydrochloride salts. An analogous sequence gave 3'-deoxytoyocamycin and/or 3'-deoxysangivamycin in approximately 80% yields from toyocamycin. Antiviral, antineoplastic, and antimetabolic effects were evaluated for the formycin compounds and 4-amino-7-beta-D-ribofuranosylpyrrolo[2,3-d]pyrimidine (tubercidin), its 5-cyano- (toyocamycin), and 5-carbamoyl-(sangivamycin) antibiotic congeners in comparison with their 2'-deoxy, 3'-deoxy, and arabino analogues. In all cases, the modified-sugar compounds were less cytotoxic than the parent antibiotics. The majority also exhibited lower antiviral potency. However, the xylo-tubercidin analogue retained potent antiherpes 1 and 2 activity with decreased cytotoxicity. Labeled metabolite studies suggested that effects of these compounds on RNA and/or protein synthesis might be more significant than interference with DNA synthesis.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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