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Usage

Uses

Used in Oncology:
Streptochlorin is used as an antineoplastic agent for treating cholangiocarcinoma. 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.
Used in Allergy Treatment:
Streptochlorin is used as an anti-allergic agent. It prevents degranulation in antigen-stimulated mast cells, as well as inhibits Syk kinase and the Src family kinases LYN and Fyn. It also reduces the secretion of TNF-α and IL-4 induced by dinitrophenyl-human serum albumin (DNP-HSA) in RBL-2H3 mast cells. Additionally, it decreases swelling and reduces scratching behavior in a mouse model of allergic dermatitis induced by dinitrofluorobenzene (DNFB).

Upstream product

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

Relevant academic research and scientific papers

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.

First discovery of pimprinine derivatives and analogs as novel potential herbicidal, insecticidal and nematicidal agents

Pimprinine and streptochlorin are indole natural products produced by many species of organisms, and they are reported to possess a wide range of biological activities, such as anticancer, antiviral, antifungal activity and so on. In this study, three series of pimprinine derivatives or analogs were efficiently synthesized under the optimized methods. Biological assays conducted at Syngenta firstly indicated the pimprinine derivatives or analogs possessed potential herbicidal and insecticidal activity, and this is highlighted by compounds 21g, 21h, 21i, 21j, 21l, 22h, 22i and 23h, they possessed significant biological activity as well as broad spectrum. Meanwhile, compounds with benzothiophene-oxazole core (21h, 22h and 23h), showed effective nematicidal activity in primary screening. Compounds 21g and 21i were identified as the most promising lead structures for further study.

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