Carbazomycin A
目录号 : GC48878
A bacterial metabolite with diverse biological activities
Cas No.:75139-39-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Carbazomycin A is a bacterial metabolite that has been found in Streptomyces and has diverse biological activities.1,2 It is active against S. aureus, T. asteroides, and T. mentagrophytes (MIC = 12.5 µg/ml for all), as well as the plant pathogenic fungus P. oryzae (MIC = 25 µg/ml). Carbazomycin A is cytotoxic to MCF-7, KB, NCI H187, and Vero cells (IC50s = 26.2, 30.1, 18.4, and 32.6 µg/ml, respectively).2
1.Sakano, K.-I., Ishimaru, K., and Nakamura, S.New antibiotics, carbazomycins A and B. I. Fermentation, extraction, purification and physico-chemical and biological propertiesJ Antibiot. (Tokyo)33(7)683-689(1980) 2.Intaraudom, C., Rachtawee, P., Suvannakad, R., et al.Antimalarial and antituberculosis substances from Streptomyces sp. BCC26924Tetrahedron67(39)7593-7597(2011)
| Cas No. | 75139-39-8 | SDF | |
| Canonical SMILES | COC(C(C)=C(C)C1=C2C3=C(C=CC=C3)N1)=C2OC | ||
| 分子式 | C16H17NO2 | 分子量 | 255.3 |
| 溶解度 | 储存条件 | -20°C | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.917 mL | 19.5848 mL | 39.1696 mL |
| 5 mM | 0.7834 mL | 3.917 mL | 7.8339 mL |
| 10 mM | 0.3917 mL | 1.9585 mL | 3.917 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
A General Carbazole Synthesis via Stitching of Indole-Ynones with Nitromethanes: Application to Total Synthesis of Carbazomycin A, Calothrixin B, and Staurosporinone
Org Lett 2019 May 3;21(9):3372-3376.PMID:31013110DOI:10.1021/acs.orglett.9b01111.
A new, one-pot domino benzannulation reaction between indole-3-ynones and various nitromethane derivatives has been explored for a general entry to diversely functionalized carbazole frameworks (28 examples). The scope of this new benzannulation has been extended to variants like 2-chloroindole-3-ynones to eventuate in chemo-differentiated 1,2,3,4-tetrasubstituted carbazoles with retention of the nitro group. The efficacy of this strategy has been demonstrated through concise total synthesis of natural products, viz. Carbazomycin A, calothrixin B, and staurosporinone (K252c).
Deprotonative Generation and Trapping of Haloaryllithium in a Batch Reactor
Org Lett 2023 May 5;25(17):3013-3017.PMID:37083303DOI:10.1021/acs.orglett.3c00800.
A method for the regioselective functionalization of haloarenes through deprotonative lithiation is disclosed. The generated haloaryllithiums were trapped in a batch reactor with a zinc chloride diamine complex to provide organozinc species without aryne formation, which reacted with electrophiles to afford the corresponding products in 38-98% yields. This method was applied to the five-step total synthesis of Carbazomycin A on a gram scale in 33% overall yield.
Diversity oriented convergent access for collective total synthesis of bioactive multifunctional carbazole alkaloids: synthesis of Carbazomycin A, carbazomycin B, hyellazole, chlorohyellazole, and clausenaline D
Org Lett 2014 Oct 17;16(20):5470-3.PMID:25296703DOI:10.1021/ol502721r.
Facile syntheses of imperative carbazole alkaloids Carbazomycin A, carbazomycin B, hyellazole, chlorohyellazole, and clausenaline D have been demonstrated starting from readily available Boc-protected 3-formylindole and dimethyl maleate. The suitably substituted aromatic rings have been designed comprising three/four significant C-C bond forming reactions. The competent Wittig reaction, selective monoalkylations, one-pot regioselective Weinreb amide formation and Boc-deprotection, well designed Grignard reactions, dehydrative intramolecular cyclizations, and Baeyer-Villiger rearrangement of aromatic aldehydes were the main features.
New antibiotics, carbazomycins A and B. I. Fermentation, extraction, purification and physico-chemical and biological properties
J Antibiot (Tokyo) 1980 Jul;33(7):683-9.PMID:7410212DOI:10.7164/antibiotics.33.683.
An unidentified Streptomyces, designated as Strain H 1051-MY 10, was proved to produce viomycin and two new antibiotics. The new antibiotics were extracted from the cultured mycelia with acetone and transferred to ethyl acetate after acetone was removed in vacuo. The extracted antibiotics were separated into two components by alumina column chromatography and named carbazomycins A and B, because both antibiotics were proved to contain a carbazole nucleus. The molecular formulae of carbazomycins A and B were determined to be C16H17NO2 and C15H15NO2, respectively. Further, carbazomycin B was methylated with diazomethane to give Carbazomycin A. Carbazomycins inhibited the growth of phytophathogenic fungi and further showed weak antibacterial and antiyeast activities.