225382-62-7

Basic information

• Product Name: 4-CHLORO-6-IODO-THIENO[3,2-D]PYRIMIDINE
• Synonyms: 4-CHLORO-6-IODO-THIENO[3,2-D]PYRIMIDINE;4-CHLORO-6-IODO-THIENO[3,...
• CAS NO: 225382-62-7
• Molecular Formula: C₆H₂ClIN₂S
• Molecular Weight: 296.52
• Mol File: 225382-62-7.mol

Chemical Properties

• Boiling Point: 369.063 °C at 760 mmHg
• Flash Point: 177.003 °C
• Appearance: /
• Density: 2.221 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.789
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-CHLORO-6-IODO-THIENO[3,2-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-6-IODO-THIENO[3,2-D]PYRIMIDINE(225382-62-7)
• EPA Substance Registry System: 4-CHLORO-6-IODO-THIENO[3,2-D]PYRIMIDINE(225382-62-7)

Safety Data

• Hazardous Substances Data: 225382-62-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLORO-6-IODO-THIENO[3,2-D]PYRIMIDINE is used as a chemical intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and properties make it a valuable component in the development of new drugs and agrochemical products.
Used in Materials Science:
In the field of materials science, 4-CHLORO-6-IODO-THIENO[3,2-D]PYRIMIDINE may be utilized for the development of novel materials with specific properties, such as electronic, optical, or magnetic characteristics, due to its halogenated thiophene derivative nature.
Used in Organic Synthesis:
4-CHLORO-6-IODO-THIENO[3,2-D]PYRIMIDINE serves as a key building block in organic synthesis, enabling the creation of a wide range of organic compounds with diverse applications in various industries.
Used in Scientific Research:
As a subject of research and interest in the scientific community, 4-CHLORO-6-IODO-THIENO[3,2-D]PYRIMIDINE may be employed in studies aimed at understanding its chemical and biological properties, as well as exploring its potential applications in various fields.

InChI:InChI=1/C6H2ClIN2S/c7-6-5-3(9-2-10-6)1-4(8)11-5/h1-2H

Upstream product

• 16269-66-2 4-chlorothieno[3,2-d]pyrimidine 
• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 
• 16285-69-1 3-(formylamino)-2-thiophenecarboxylic acid methyl ester 
• 16234-10-9 3H-thieno[3,2-d]pyrimidin-4-one 

Downstream Products

• 853679-53-5 (4-benzyl-piperazin-1-yl)-6-iodothieno[3,2-d]pyrimidine 
• 1337875-44-1 C₁₅H₁₁N₃O₃S₂ 
• 1337875-45-2 C₁₅H₁₁N₃O₃S₂ 
• 1337875-46-3 C₁₆H₁₃N₃O₃S₂ 
• 1337875-47-4 2-((6-(4-acetamidophenyl)thieno[3,2-d]pyrimidin-4-yl)thio)acetic acid 
• 1337875-48-5 C₁₆H₁₃ClN₂O₂S₂ 
• 1337875-54-3 2-((6-(4-chlorophenyl)thieno[3,2-d]pyrimidin-4-yl)oxy)acetic acid 
• 1337875-55-4 C₁₆H₁₃N₃O₄S 
• 1337875-59-8 C₁₄H₁₀ClN₃O₂S 
• 1337875-60-1 C₁₅H₁₂ClN₃O₂S 
• 1337875-36-1 C₁₄H₉FN₂O₂S₂ 
• 1337875-37-2 2-((6-(4-chlorophenyl)thieno[3,2-d]pyrimidin-4-yl)thio)acetic acid 
• 1337875-38-3 C₁₅H₁₂N₂O₂S₂ 
• 1337875-39-4 C₁₅H₁₂N₂O₂S₂ 

Relevant articles and documents

Macrocyclization as a Source of Desired Polypharmacology. Discovery of Triple PI3K/mTOR/PIM Inhibitors

The PI3K/AKT/mTOR and PIM kinase pathways contribute to the development of several hallmarks of cancer. Cotargeting of these pathways has exhibited promising synergistic therapeutic effects in liquid and solid tumor types. To identify molecules with combined activities, we cross-screened our collection of PI3K/(±mTOR) macrocycles (MCXs) and identified the MCX thieno[3,2-d]pyrimidine derivative 2 as a moderate dual PI3K/PIM-1 inhibitor. We report the medicinal chemistry exploration and biological characterization of a series of thieno[3,2-d]pyrimidine MCXs, which led to the discovery of IBL-302 (31), a potent, selective, and orally bioavailable triple PI3K/mTOR/PIM inhibitor. IBL-302, currently in late preclinical development (AUM302), has recently demonstrated efficacy in neuroblastoma and breast cancer xenografts. Additionally, during the course of our experiments, we observed that macrocyclization was essential to obtain the desired multitarget profile. As a matter of example, the open precursors 35-37 were inactive against PIM whereas MCX 28 displayed low nanomolar activity.

Hinge Binder Scaffold Hopping Identifies Potent Calcium/Calmodulin-Dependent Protein Kinase Kinase 2 (CAMKK2) Inhibitor Chemotypes

CAMKK2 is a serine/threonine kinase and an activator of AMPK whose dysregulation is linked with multiple diseases. Unfortunately, STO-609, the tool inhibitor commonly used to probe CAMKK2 signaling, has limitations. To identify promising scaffolds as starting points for the development of high-quality CAMKK2 chemical probes, we utilized a hinge-binding scaffold hopping strategy to design new CAMKK2 inhibitors. Starting from the potent but promiscuous disubstituted 7-azaindole GSK650934, a total of 32 compounds, composed of single-ring, 5,6-, and 6,6-fused heteroaromatic cores, were synthesized. The compound set was specifically designed to probe interactions with the kinase hinge-binding residues. Compared to GSK650394 and STO-609, 13 compounds displayed similar or better CAMKK2 inhibitory potency in vitro, while compounds 13g and 45 had improved selectivity for CAMKK2 across the kinome. Our systematic survey of hinge-binding chemotypes identified several potent and selective inhibitors of CAMKK2 to serve as starting points for medicinal chemistry programs.

A Chemical Probe for Dark Kinase STK17B Derives Its Potency and High Selectivity through a Unique P-Loop Conformation

STK17B is a member of the death-associated protein kinase family and has been genetically linked to the development of diverse diseases. However, the role of STK17B in normal and disease pathology is poorly defined. Here, we present the discovery of thieno[3,2-d] pyrimidine SGC-STK17B-1 (11s), a high-quality chemical probe for this understudied "dark"kinase. 11s is an ATP-competitive inhibitor that showed remarkable selectivity over other kinases including the closely related STK17A. X-ray crystallography of 11s and related thieno[3,2-d]pyrimidines bound to STK17B revealed a unique P-loop conformation characterized by a salt bridge between R41 and the carboxylic acid of the inhibitor. Molecular dynamic simulations of STK17B revealed the flexibility of the P-loop and a wide range of R41 conformations available to the apo-protein. The isomeric thieno[2,3-d]pyrimidine SGC-STK17B-1N (19g) was identified as a negative control compound. The >100-fold lower activity of 19g on STK17B was attributed to the reduced basicity of its pyrimidine N1.

Identification and SAR of a new series of thieno[3,2-d]pyrimidines as Tpl2 kinase inhibitors

We report here the synthesis and SAR of a new series of thieno[3,2-d]pyrimidines as potent Tpl2 kinase inhibitors. The proposed binding mode suggests the potential flipped binding mode depending on the substitution. Biacore studies show evidence of binding of these molecules to the protein kinase. The kinome inhibition profile of these molecules suggests good selectivity.

B-Raf kinase inhibitors: Hit enrichment through scaffold hopping

In continuation of our efforts toward hit identification and optimization for a B-Raf kinase project, we have employed a scaffold hopping strategy. The original HTS hit scaffold pyrazolo[1,5-a]pyrimidine was replaced with different thienopyrimidine and th

THIENOPYRIMIDINES, THIENOPYRIDINES, AND PYRROLOPYRIMIDINES AS B-RAF INHIBITORS

The present invention relates to compounds of formula la: and pharmaceutically acceptable salts thereof. The thieno[3,2-d]pyrimidine, thieno[2,3-d]pyrimidine, thieno[3,2-b]pyridine, thieno[2,3-b]pyridine, and pyrrolo[2,3-d]pyrimidine compounds selectively

N-arylalkyl-thienopyrimidin-4-amines and analogs as activators of caspases and inducers of apoptosis and the use thereof

Disclosed are N-arylalkyl-thienopyrimidin-4-amines and analogs thereof, represented by the Formula I: wherein Ar, R1, R3, R4, R10-R12 and n are defined herein. The present invention relates to the dis

AKT PROTEIN KINASE INHIBITORS

The present invention provides compounds, including resolved enantiomers, diastereomers, solvates and pharmaceutically acceptable salts thereof, comprising the Formula: A-L-CR where CR is a cyclical core group, L is a linking group and A is as defined herein. Also provided are methods of using the compounds of this invention as AKT protein kinase inhibitors and for the treatment of hyperproliferative diseases such as cancer.