WS-9659 B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01653 |
| CAS | 123313-61-1 |
| Molecular Weight | 366.9 |
| Molecular Formula | C22H23ClN2O |
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Description
WS-9659 B is a testosterone 5 alpha-reductase inhibitor isolated from Streptomyces sp. No. 9659. It exhibits weak activity against gram-positive bacteria.
Specification
| Synonyms | WS-9659B; WS 9659 B |
| IUPAC Name | 2-chloro-5-[(2,4,4-trimethylcyclohexen-1-yl)methyl]phenazin-1-one |
| Canonical SMILES | CC1=C(CCC(C1)(C)C)CN2C3=CC=CC=C3N=C4C2=CC=C(C4=O)Cl |
| InChI | InChI=1S/C22H23ClN2O/c1-14-12-22(2,3)11-10-15(14)13-25-18-7-5-4-6-17(18)24-20-19(25)9-8-16(23)21(20)26/h4-9H,10-13H2,1-3H3 |
| InChI Key | UTTPOQJPJBHXNA-UHFFFAOYSA-N |
Properties
| Appearance | Dark Blue Crystal |
| Melting Point | 152-153°C |
Reference Reading
1. WS-9659 A and B, novel testosterone 5 alpha-reductase inhibitors isolated from a Streptomyces. III. Biological characteristics and pharmacological characteristics
O Nakayama, H Arakawa, M Yagi, M Tanaka, S Kiyoto, M Okuhara, M Kohsaka J Antibiot (Tokyo). 1989 Aug;42(8):1235-40. doi: 10.7164/antibiotics.42.1235.
WS-9659 A, a novel phenazine, produced by a Streptomyces sp., had testosterone 5 alpha-reductase inhibition activity on rat, dog and human prostates. However, WS-9659 A did not show any inhibitory activities for aldose reductase on rabbit lenses and lactate dehydrogenase on pig hearts. WS-9659 A was a competitive inhibitor against testosterone 5 alpha-reductase on rat prostates by use of testosterone as a substrate. Radio receptor binding assay of androgen receptor of rat prostates revealed that WS-9659 A had no affinity for this receptor. WS-9659 A was tested subcutaneously in immature castrated rats to confirm its effect on the growth of the ventral prostates induced by testosterone propionate.
2. WS-9659 A and B, novel testosterone 5 alpha-reductase inhibitors isolated from a Streptomyces. II. Structural elucidation of WS-9659 A and B
O Nakayama, N Shigematsu, A Katayama, S Takase, S Kiyoto, M Hashimoto, M Kohsaka J Antibiot (Tokyo). 1989 Aug;42(8):1230-4. doi: 10.7164/antibiotics.42.1230.
On the basis of spectroscopic and chemical evidence, the structures of WS-9659 A and B isolated as inhibitors of testosterone 5 alpha-reductase from a Streptomyces have been established as 1 and 2, respectively. The reductase inhibitory activities of the derivatives 5 and 6, and degradation products 3 and 8 were considerably less active and substantially inactive, respectively.
3. Synthesis and Cytotoxic Evaluation of N-Alkyl-2-halophenazin-1-ones
Haruki Kohatsu, Shogo Kamo, Masateru Furuta, Shusuke Tomoshige, Kouji Kuramochi ACS Omega. 2020 Oct 16;5(42):27667-27674. doi: 10.1021/acsomega.0c04253. eCollection 2020 Oct 27.
In this study, the synthesis of N-alkyl-2-halophenazin-1-ones has been established. Six N-alkyl-2-halophenazin-1-ones, including WS-9659 B and marinocyanins A and B, were synthesized by the direct oxidative condensation of 4-halo-1,2,3-benzenetriol with the corresponding N-alkylbenzene-1,2-diamines. One of the most significant features of the present method is that it can be successfully applied to the synthesis of N-alkyl-2-chlorophenazin-1-ones. The traditional chlorination of N-alkyl-phenazin-1-ones with N-chlorosuccinimide selectively occurs at the 4-position to afford the undesired N-alkyl-4-chlorophenazin-1-ones. Our synthetic route successfully circumvents this problem, culminating in the first chemical synthesis of WS-9659 B. The cytotoxicity of six N-alkyl-2-halophenazin-1-ones and three N-alkylphenazin-1-ones against human promyelocytic leukemia HL-60, human lung cancer A549, and normal MRC-5 cells was evaluated. Among the compounds tested in this study, 2-chloropyocyanin possesses significant selectivity toward A549 cells. The cytotoxic evaluation provides structural insights into the potency and selectivity of these compounds for cancer cells.
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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 ╳
