73425-13-5

Basic information

• Product Name: 5-FLUORO-1,3-DIHYDRO-INDOLE-2-THIONE
• Synonyms: 5-FLUORO-1,3-DIHYDRO-INDOLE-2-THIONE;5-fluoroindoline-2-thione
• CAS NO: 73425-13-5
• Molecular Formula: C₈H₆FNS
• Molecular Weight: 167.2033432
• Mol File: 73425-13-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 240.7°C at 760 mmHg
• Flash Point: 99.4°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 0.0374mmHg at 25°C
• Refractive Index: 1.659
• CAS DataBase Reference: 5-FLUORO-1,3-DIHYDRO-INDOLE-2-THIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-FLUORO-1,3-DIHYDRO-INDOLE-2-THIONE(73425-13-5)
• EPA Substance Registry System: 5-FLUORO-1,3-DIHYDRO-INDOLE-2-THIONE(73425-13-5)

Safety Data

• Hazardous Substances Data: 73425-13-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H6FNS/c9-6-1-2-7-5(3-6)4-8(11)10-7/h1-3H,4H2,(H,10,11)

Upstream product

• 56341-41-4 5-fluoroindol-2(3H)-one 
• 443-69-6 5-fluoro-1H-indole-2,3-dione 

Downstream Products

• 73425-89-5 Ethyl-(6-fluoro-2,3,4,9-tetrahydro-thiopyrano[2,3-b]indol-4-ylmethyl)-amine; compound with oxalic acid 
• 73425-87-3 (6-Fluoro-2,3,4,9-tetrahydro-thiopyrano[2,3-b]indol-4-ylmethyl)-methyl-amine; compound with oxalic acid 

Relevant articles and documents

Design and synthesis of indoleamine 2,3-dioxygenase 1 inhibitors and evaluation of their use as anti-tumor agents

Indoleamine 2,3-dioxygenase (IDO) 1 is the key enzyme for regulating tryptophan metabolism and is an important target for interrupting tumor immune escape. In this study, we designed four series of compounds as potential IDO1 inhibitors by attaching various fragments or ligands to indole or phenylimidazole scaffolds to improve binding to IDO1. The compounds were synthesized and their inhibitory activities against IDO1 and tryptophan 2,3-dioxygenase were evaluated. The cytotoxicities of the compounds against two tumor cell lines were also determined. Two compounds with a phenylimidazole scaffold (DX-03-12 and DX-03-13) showed potent IDO1 inhibition with IC50 values of 0.3–0.5 μM. These two IDO1 inhibitors showed low cell cytotoxicity, which indicated that they may exert their anti-tumor effect via immune modulation. Compound DX-03-12 was investigated further by determining the in vivo pharmacokinetic profile and anti-tumor efficacy. The pharmacokinetic study revealed that DX-03-12 had satisfactory properties in mice, with rapid absorption, moderate plasma clearance (～36% of hepatic blood flow), acceptable half-life (～4.6 h), and high oral bioavailability (～96%). Daily oral administration of 60 mg/kg of compound DX-03-12 decreased tumor growth by 72.2% after 19 days in a mouse melanoma cell B16-F10 xenograft model compared with the untreated control. Moreover, there was no obvious weight loss in DX-03-12-treated mice. In conclusion, compound DX-03-12 is a potent lead compound for developing IDO1 inhibitors and anti-tumor agents.

Metal-free hydroamination of alkynes: A mild and concise synthesis of thiazolo[3,2- a ]indoles and their cytotoxic activity

A metal-free, mild and efficient method for the synthesis of thiazolo[3,2- a ]indoles has been developed starting from indoline-2-thiones. The reaction methodology involves first the formation of thermally labile 2-(prop-2-ynylthio)-1 H -indole intermedia

Studies on fused indoles. II. Structural modifications and analgesic activity of 4-aminomethyltetrahydrothiopyrano[2,3-b]indoles

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