1799610-89-1

Basic information

• Product Name: 5-bromo-4-chloro-6-iodothieno[2,3-d]pyrimidine
• Synonyms: 5-bromo-4-chloro-6-iodothieno[2,3-d]pyrimidine;Thieno[2,3-d]pyrimidine, 5-bromo-4-chloro-6-iodo-
• CAS NO: 1799610-89-1
• Molecular Formula: C6HBrClIN2S
• Molecular Weight: 375.41201
• EINECS: -0
• Mol File: 1799610-89-1.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 421.8±40.0 °C(Predicted)
• Appearance: /
• Density: 2.508±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: -0.99±0.40(Predicted)
• CAS DataBase Reference: 5-bromo-4-chloro-6-iodothieno[2,3-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo-4-chloro-6-iodothieno[2,3-d]pyrimidine(1799610-89-1)
• EPA Substance Registry System: 5-bromo-4-chloro-6-iodothieno[2,3-d]pyrimidine(1799610-89-1)

Safety Data

• Hazardous Substances Data: 1799610-89-1(Hazardous Substances Data)

Usage

Description

5-bromo-4-chloro-6-iodothieno[2,3-d]pyrimidine is a heterocyclic chemical compound with a molecular formula of C6H2BrClIN2S. It features a thiophene ring fused to a pyrimidine ring, with bromine, chlorine, and iodine substituents at specific positions. 5-bromo-4-chloro-6-iodothieno[2,3-d]pyrimidine exhibits potential pharmaceutical activity and is of significant interest to researchers in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
5-bromo-4-chloro-6-iodothieno[2,3-d]pyrimidine is used as a building block in the synthesis of various pharmaceutical compounds, including potential anti-cancer and anti-inflammatory drugs. Its unique structure and properties make it a promising candidate for drug discovery and development.
Used in Chemical Industry:
5-bromo-4-chloro-6-iodothieno[2,3-d]pyrimidine is also used as a reagent in organic synthesis for the development of novel chemical compounds. Its versatility and potential applications in creating new molecules contribute to its importance in the chemical industry.

Upstream product

• 4651-82-5 2-amino-3-cyanothiophene 
• 128-08-5 N-Bromosuccinimide 
• 552295-08-6 4-chloro-6-iodo-thieno[2,3-d]pyrimidine 
• 14080-50-3 thieno[2,3-d]pyrimidin-4(3H)one 

Downstream Products

• 1799633-27-4 (2R)-2-{[(5S_a)-5-{3-chloro-2-methyl-4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}-6-(5-fluorofuran-2-yl)thieno[2,3-d]pyrimidin-4-yl]oxy}-3-(2-{[1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl]methoxy}phenyl)propanoic acid 

Relevant articles and documents

Discovery of S64315, a Potent and Selective Mcl-1 Inhibitor

Myeloid cell leukemia 1 (Mcl-1) has emerged as an attractive target for cancer therapy. It is an antiapoptotic member of the Bcl-2 family of proteins, whose upregulation in human cancers is associated with high tumor grade, poor survival, and resistance to chemotherapy. Here we report the discovery of our clinical candidate S64315, a selective small molecule inhibitor of Mcl-1. Starting from a fragment derived lead compound, we have conducted structure guided optimization that has led to a significant (3 log) improvement of target affinity as well as cellular potency. The presence of hindered rotation along a biaryl axis has conferred high selectivity to the compounds against other members of the Bcl-2 family. During optimization, we have also established predictive PD markers of Mcl-1 inhibition and achieved both efficient in vitro cell killing and tumor regression in Mcl-1 dependent cancer models. The preclinical candidate has drug-like properties that have enabled its development and entry into clinical trials.

Macrocyclic MCL-1 inhibitors and methods of use

The present disclosure provides for compounds of Formula (I) wherein A2, A3, A4, A6, A7, A8, A15, RA, R5, R9, R10A, R10B, R11, R12, R13, R14, R16, W, X, and Y have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, that are useful as agents for the treatment of diseases and conditions, including cancer. Also provided are pharmaceutical compositions comprising compounds of Formula (I).

Structure-guided discovery of a selective mcl-1 inhibitor with cellular activity

Myeloid cell leukemia 1 (Mcl-1), an antiapoptotic member of the Bcl-2 family of proteins, whose upregulation when observed in human cancers is associated with high tumor grade, poor survival, and resistance to chemotherapy, has emerged as an attractive target for cancer therapy. Here, we report the discovery of selective small molecule inhibitors of Mcl-1 that inhibit cellular activity. Fragment screening identified thienopyrimidine amino acids as promising but nonselective hits that were optimized using nuclear magnetic resonance and X-ray-derived structural information. The introduction of hindered rotation along a biaryl axis has conferred high selectivity to the compounds, and cellular activity was brought on scale by offsetting the negative charge of the anchoring carboxylate group. The obtained compounds described here exhibit nanomolar binding affinity and mechanism-based cellular efficacy, caspase induction, and growth inhibition. These early research efforts illustrate drug discovery optimization from thienopyrimidine hits to a lead compound, the chemical series leading to the identification of our more advanced compounds S63845 and S64315.