165947-48-8

Basic information

• Product Name: 5-(TERT-BUTOXYCARBONYL)-4,5,6,7-TETRAHYDROTHIENO[3,2-C]PYRIDINE-2-CARBOXYLIC ACID
• Synonyms: 5-(TERT-BUTOXYCARBONYL)-4,5,6,7-TETRAHYDROTHIENO[3,2-C]PYRIDINE-2-CARBOXYLIC ACID;5-BOC-4,5,6,7-TETRAHYDROTHIENO[3,2-C]PYRIDINE-2-CARBOXYLIC ACID;2-c]pyridine-2-carboxylic acid;5-(tert-butoxycarbonyl)-4;5-(tert-butoxycarbonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-;5-[(tert-butoxy)carbonyl]-4H,5H,6H,7H-thieno[3,2- c]pyridine-2-carboxylic acid;5-[(2-methylpropan-2-yl)oxycarbonyl]-6,7-dihydro-4H-thieno[3,2-c]pyridine-2-carboxylic acid
• CAS NO: 165947-48-8
• Molecular Formula: C₁₃H₁₇NO₄S
• Molecular Weight: 283.34
• Product Categories: CHIRAL CHEMICALS
• Mol File: 165947-48-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 453.157 °C at 760 mmHg
• Flash Point: 227.861 °C
• Appearance: /
• Density: 1.309 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.581
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.86±0.20(Predicted)
• CAS DataBase Reference: 5-(TERT-BUTOXYCARBONYL)-4,5,6,7-TETRAHYDROTHIENO[3,2-C]PYRIDINE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(TERT-BUTOXYCARBONYL)-4,5,6,7-TETRAHYDROTHIENO[3,2-C]PYRIDINE-2-CARBOXYLIC ACID(165947-48-8)
• EPA Substance Registry System: 5-(TERT-BUTOXYCARBONYL)-4,5,6,7-TETRAHYDROTHIENO[3,2-C]PYRIDINE-2-CARBOXYLIC ACID(165947-48-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 165947-48-8(Hazardous Substances Data)

Usage

General Description

5-(tert-butoxycarbonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid is a chemical compound with the molecular formula C15H19NO4S. It is a derivative of thieno[3,2-c]pyridine which has a tert-butoxycarbonyl (Boc) protecting group attached to the nitrogen atom and a carboxylic acid group attached to the carbon atom. 5-(TERT-BUTOXYCARBONYL)-4,5,6,7-TETRAHYDROTHIENO[3,2-C]PYRIDINE-2-CARBOXYLIC ACID is used in organic synthesis as a building block for the preparation of various pharmaceuticals and other biologically active molecules. It is also commonly used in the development of new drugs and as a research tool for the study of various biological processes.

InChI:InChI=1/C13H17NO4S/c1-13(2,3)18-12(17)14-5-4-9-8(7-14)6-10(19-9)11(15)16/h6H,4-5,7H2,1-3H3,(H,15,16)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 116118-98-0 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid 
• 110-54-3 hexane 
• 949922-62-7 2-bromo-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylic acid tert-butyl ester 
• 124-38-9 carbon dioxide 
• 28783-41-7 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride 
• 885275-20-7 tert-butyl 4-chloro-5-formyl-3,6-dihydropyridine-1(2H)-carboxylate 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 623564-30-7 5-(tert-butyl) 2-ethyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate 

Downstream Products

• 1135123-74-8 5-(tert-butyl) 2-methyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate 
• 1013210-86-0 2-carbamoyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine 
• 197238-08-7 t-butyl [4-[2-[[[5-(t-butoxycarbonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl]carbonyl]-N-methylamino]-1-hydroxyethyl]phenyl] oxyacetate 

Relevant articles and documents

Synthesis, characterization and anticancer activity of 5-substituted 4,5,6,7-tetrahydro-N-(tetrahydro-2H-pyran-4-yl)thieno[3,2-c]pyridine-2-carboxamide derivatives

4,5,6,7-Tetrahydrothieno pyridine (THTP) and their derivatives are an important heterocyclic compounds that exhibits various biological activities viz.,antimicrobial activity, antileishmanial activity, antiarrhythmic activity, antiinflammatory activity, antihyperlipidemic activity, antidepressant activity, anticancer activity, antiplatelet activity and antidiabetic etc. The present study describes the synthesis, characterization and in vitro cytotoxic potential against human lung carcinoma of some novel derivatives of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine (7A-M) with benzylic and amide substitution on the nitrogen atom of tetrahydro theino pyridine ring. The synthetic steps involves (i) Vilsmeyer protocol in step 1 (ii) formation of tetrahydothieno[3,2-c]pyridine ring in presence of 2-mercaptoacetate in step 2 (iii) alkaline hydrolysis followed by amide coupling with tetrahydro-2H-pyran-4-amine in step 3 and step 4. The newly synthesized compounds 7A-M was sufficiently characterized by 1 H NMR, IR and mass techniques. Furthermore, these derivatives were screened for their in vitro cytotoxic potential against human lung carcinoma (HCT-116) cell line using the MTT assay. Compound 7B (IC50: 69.52 μg) and compound 7K (IC50: 66.35 μg) exhibited significant activity at micro molar concentration when compared to standard drug camptothecin.

Discovery of 2-substituted-N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide as potent and selective protein arginine methyltransferases 5 inhibitors: Design, synthesis and biological evaluation

Protein arginine methyltransferases 5 (PRMT5) represents an attractive drug target in epigenetic field for the treatment of leukemia and lymphoma. Here, a series of N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)amide derivatives targeting PRMT5 were designed with structure-based approach and synthesized. Among them, compound 46 showed potent and selective PRMT5 inhibition activity with an IC50 of 8.5 nM, which was approximately equivalent with the phase I clinical trial PRMT5 inhibitor GSK-3326595 (IC50 = 5.5 nM). Compound 46 also displayed pronounced anti-proliferative activity in MV4-11 cells (GI50 = 18 nM) and antitumor activity in MV4-11 mouse xenografts model. This molecule can serve as an excellent tool compound for probing the biological function of PRMT5.

Compound with platelet aggregation inhibitor activity

A compound represented by the general formula (I) and a pharmaceutically acceptable salt and solvate thereof having an effect for inhibiting the agglutination of platelets is disclosed: STR1 wherein R1 represents a group --W--(CH2)i --COOR3, R2 represents a hydrogen atom or a group --W--(CH2)i --COOR3 or --OR4, X represents --CH= or --N=, Y represents (i) a group --(CO)k --N(R5)--Z--, wherein Z represents a bond or a group --(CH2)m --CO-- or a group --(CH2)m --CHR6 --, (ii) a group --(CH2)m --N(R5)--(CO)k --, or (iii) a group --(CO)k -Het, wherein Het represents a five- or six-membered heterocyclic ring comprising a nitrogen atom, A represents (i) the following groups (III) or (IV) STR2 B represents a bond, C1-6 alkylene or C2-6 alkenylen.