Melithiazol D
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| Category | Antibiotics |
| Catalog number | BBF-01909 |
| CAS | 248938-46-7 |
| Molecular Weight | 424.58 |
| Molecular Formula | C20H28N2O4S2 |
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Description
Melithiazol D is an antibiotic produced by Melittangium lichenicila Mel26, Archangium gephyra Ar 7747 and Myxococcus stipitatus Mx s 64. It is a β-methoxyacrylate (MOA) inhibitor with strong anti-agent activity.
Specification
| IUPAC Name | methyl (2E,6E)-3,5-dimethoxy-4-methyl-7-[2-(2-propan-2-yl-4,5-dihydro-1,3-thiazol-4-yl)-1,3-thiazol-4-yl]hepta-2,6-dienoate |
| Canonical SMILES | CC(C)C1=NC(CS1)C2=NC(=CS2)C=CC(C(C)C(=CC(=O)OC)OC)OC |
| InChI | InChI=1S/C20H28N2O4S2/c1-12(2)19-22-15(11-28-19)20-21-14(10-27-20)7-8-16(24-4)13(3)17(25-5)9-18(23)26-6/h7-10,12-13,15-16H,11H2,1-6H3/b8-7+,17-9+ |
| InChI Key | MKHXEKLNLZKVLK-ITDUAQOSSA-N |
Properties
| Appearance | Oil |
| Boiling Point | 557.5±50.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Concise syntheses of cystothiazoles A, C, D, and melithiazol B
Yuki Iwaki, Hiroyuki Akita Chem Pharm Bull (Tokyo). 2007 Nov;55(11):1610-4. doi: 10.1248/cpb.55.1610.
A convergent synthesis of cystothiazoles C 1 and D 3 was achieved based on Julia coupling between the functionalized aldehyde 5b, corresponding to left half of the final molecule, and aryl sulfone 6 or 7, bearing a bithiazole moiety, corresponding to right half. Methylation of 1 and 3 gave cystothiazole A 2 and melithiazol B 4, respectively. The overall yield (5 steps from (2R,3S)-3-methylpent-4-yne-1,2-diol 10; 57%) of 5b via the present route was improved in comparison to that of the previously reported functionalized aldehyde 5a (7 steps from 10; 13%). By applying the modified Julia coupling method, selectivity (6E/6Z=20 : 1-26 : 1) toward the (6E)-form of the coupled products (15 or 19) against the corresponding (6Z)-form was improved in comparison to the Wittig method (6E/6Z=4 : 1-6.9 : 1).
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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 ╳
