120191-51-7

Basic information

• Product Name: Streptochlorin
• Synonyms: Streptochlorin;3-(4-Chloro-5-oxazolyl)-1H-indole;Antibiotic SF 2583A;SF 2583A
• CAS NO: 120191-51-7
• Molecular Formula: C11H7ClN2O
• Molecular Weight: 218.63908
• Mol File: 120191-51-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Streptochlorin(CAS DataBase Reference)
• NIST Chemistry Reference: Streptochlorin(120191-51-7)
• EPA Substance Registry System: Streptochlorin(120191-51-7)

Safety Data

• Hazardous Substances Data: 120191-51-7(Hazardous Substances Data)

Usage

Description

Streptochlorin is a bacterial metabolite originally isolated from Streptomyces sp. SF2583 that has diverse biological activities, including antiangiogenic, antiproliferative, and anti-allergic properties. It inhibits TNF-α-induced NF-κB transcriptional activity and decreases proliferation of human umbilical vein endothelial cells (HUVECs) when used at concentrations ranging from 5 to 20 μM. Streptochlorin (12 μg/ml) decreases viability of, as well as induces apoptosis and increases the production of reactive oxygen species (ROS) in, Hep3B human hepatocellular carcinoma cells. It does not induce cytotoxicity in RBL-2H3 mast cells at concentrations up to 100 μM. Streptochlorin prevents degranulation in antigen-stimulated mast cells, as well as inhibits Syk kinase and the Src family kinases LYN and Fyn and reduces the secretion of TNF-α and IL-4 induced by dinitrophenyl-human serum album (DNP-HSA) in RBL-2H3 mast cells. It also decreases swelling and reduces scratching behavior in a mouse model of allergic dermatitis induced by dinitrofluorobenzene (DNFB).

Uses

Streptochlorin is an antineoplastic agent and a potential chemotherapeutic agent for treating cholangiocarcinoma.

Upstream product

• 1435936-64-3 C₁₆H₁₆N₂O₃ 
• 57476-50-3 1-tert-butoxycarbonyl-3-formylindole 
• 120-72-9 indole 
• 942-24-5 3-methoxycarbonylindole 
• 120191-50-6 5-(1H-indol-3-yl)oxazole 
• 80360-20-9 1-(phenylsulfonyl)indole-3-carbaldehyde 
• 1383483-14-4 4-chloro-5-(1-(phenylsulfonyl)-1H-indol-3-yl)oxazole 
• 1383483-13-3 5-(1-(phenylsulfonyl)-1H-indol-3-yl)oxazole 
• 487-89-8 Indole-3-carboxaldehyde 

Relevant articles and documents

Oxazole Synthesis by Sequential Asmic-Ester Condensations and Sulfanyl-Lithium Exchange-Trapping

Oxazoles are rapidly assembled through a sequential deprotonation-condensation of Asmic, anisylsulfanylmethylisocyanide, with esters followed by sulfanyl-lithium exchange-trapping. Deprotonating Asmic affords a metalated isocyanide that efficiently traps esters to afford oxazoles bearing a versatile C-4 anisylsulfanyl substituent. Interchange of the anisylsulfanyl substituent is readily achieved through a first-in-class sulfur-lithium exchange-electrophilic trapping sequence whose versatility is illustrated in the three-step synthesis of the bioactive natural product streptochlorin.

Preparation method and application of natural product Streptochlorin and derivatives thereof

The invention discloses a preparation method of a derivative of a natural product Streptochlorin. The invention also discloses an application of the natural product Streptochlorin and the derivative thereof in killing pathogenic bacteria of crops. The natural product Streptochlorin and the derivative thereof have the advantages that the bactericidal activity is good, can be applied to crop diseases caused by fungi, bacteria and viruses, and show efficient and/or broad-spectrum bactericidal activity.

Synthesis and fungicidal activity of novel pimprinine analogues

A simple and efficient synthetic protocol for 5-(3-indolyl)-oxazoles has been developed and further used to synthesize a series of novel analogues of natural product pimprinine. All new compounds were identified by 1H NMR, high resolution mass