387819-41-2

Basic information

• Product Name: 7-chloro-Thieno[3,2-b]pyridine-2-carboxaldehyde
• Synonyms: 7-chloro-Thieno[3,2-b]pyridine-2-carboxaldehyde;7-chlorothieno[3,2-b]pyridine-2-carbaldehyde
• CAS NO: 387819-41-2
• Molecular Formula: C₈H₄ClNOS
• Molecular Weight: 197.64
• Mol File: 387819-41-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-chloro-Thieno[3,2-b]pyridine-2-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 7-chloro-Thieno[3,2-b]pyridine-2-carboxaldehyde(387819-41-2)
• EPA Substance Registry System: 7-chloro-Thieno[3,2-b]pyridine-2-carboxaldehyde(387819-41-2)

Safety Data

• Hazardous Substances Data: 387819-41-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-chloro-Thieno[3,2-b]pyridine-2-carboxaldehyde serves as an intermediate in the synthesis of pharmaceutical compounds, contributing to the development of drugs for a range of diseases. Its aldehyde group allows for further chemical reactions and modifications, enhancing the compound's therapeutic potential.
Used in Agrochemical Industry:
In the agrochemical sector, 7-chloro-Thieno[3,2-b]pyridine-2-carboxaldehyde is utilized as a building block for the production of insecticides and herbicides. Its chlorine atom and aldehyde functionality provide a foundation for creating effective and targeted pest control agents.
Used in Chemical Research and Development:
7-chloro-Thieno[3,2-b]pyridine-2-carboxaldehyde is a valuable tool in chemical research and development due to its unique structure and functional groups. It can be employed in the exploration of novel chemical reactions and the synthesis of new compounds with potential applications in various industries.
Safety Precautions:
Given its potential hazards, 7-chloro-Thieno[3,2-b]pyridine-2-carboxaldehyde should be handled with care, adhering to proper safety precautions and guidelines. This includes using appropriate personal protective equipment, working in well-ventilated areas, and following established protocols to minimize risks during its use and manipulation.

Upstream product

• 69627-02-7 thieno[3,2-b]pyridin-7-ol 
• 69627-03-8 7-chlorothieno[3,2-b]pyridine 
• 68-12-2 N,N-dimethyl-formamide 

Relevant articles and documents

Discovery of Novel Central Nervous System Penetrant Metabotropic Glutamate Receptor Subtype 2 (mGlu2) Negative Allosteric Modulators (NAMs) Based on Functionalized Pyrazolo[1,5- a]pyrimidine-5-carboxamide and Thieno[3,2- b]pyridine-5-carboxamide Cores

A scaffold hopping exercise from a monocyclic mGlu2 NAM with poor rodent PK led to two novel heterobicyclic series of mGlu2 NAMs based on either a functionalized pyrazolo[1,5-a]pyrimidine-5-carboxamide core or a thieno[3,2-b]pyridine-5-carboxamide core. These novel analogues possess enhanced rodent PK, while also maintaining good mGlu2 NAM potency, selectivity (versus mGlu3 and the remaining six mGlu receptors), and high CNS penetration. Interestingly, SAR was divergent between the new 5,6-heterobicyclic systems.

BIOMARKER-BASED THERAPEUTIC COMPOSITION

The present invention provides an anticancer agent for treating a patient who is resistant to a protein kinase inhibitor, the anticancer agent comprising, as an active ingredient, a thienopyridine derivative compound or a pharmaceutically acceptable salt thereof. Here, the patient may be a patient carrying active RON. In addition, the patient may be a patient carrying normal KRAS. In addition, the anticancer agent may be applied to a patient who is resistant to an EGFR inhibitor. In particular, the anticancer agent may be usefully used to treat a patient who is resistant to the therapeutic agent cetuximab.

Piperidine compound and preparation method and medical application thereof

The invention discloses a piperidine compound shown as a formula (I) and a preparation method and medical application thereof, and particularly relates to a piperidine USP7 inhibitor compound or pharmaceutically acceptable salt or ester or solvate thereof and a preparation method and application of the piperidine USP7 inhibitor compound or pharmaceutically acceptable salt or ester or solvate thereof. The compound provided by the invention can inhibit the activity of USP7 enzyme, has very good selectivity and druggability, and can be used for preparing medicines for preventing or treating tumor diseases or virus infectious diseases.

Discovery of Potent, Selective, and Orally Bioavailable Inhibitors of USP7 with in Vivo Antitumor Activity

USP7 is a promising target for cancer therapy as its inhibition is expected to decrease function of oncogenes, increase tumor suppressor function, and enhance immune function. Using a structure-based drug design strategy, a new class of reversible USP7 inhibitors has been identified that is highly potent in biochemical and cellular assays and extremely selective for USP7 over other deubiquitinases. The succinimide was identified as a key potency-driving motif, forming two strong hydrogen bonds to the allosteric pocket of USP7. Redesign of an initial benzofuran-amide scaffold yielded a simplified ether series of inhibitors, utilizing acyclic conformational control to achieve proper amine placement. Further improvements were realized upon replacing the ether-linked amines with carbon-linked morpholines, a modification motivated by free energy perturbation (FEP+) calculations. This led to the discovery of compound 41, a highly potent, selective, and orally bioavailable USP7 inhibitor. In xenograft studies, compound 41 demonstrated tumor growth inhibition in both p53 wildtype and p53 mutant cancer cell lines, demonstrating that USP7 inhibitors can suppress tumor growth through multiple different pathways.

IMPROVED METHODS FOR PREPARING BENZOFUSED HETEROARYL AMIDE DERIVATIVES OF THIENOPYRIDINES

The invention relates to methods for preparing compounds of formulae (I) and (XI): or pharmaceutically acceptable salts or solvates thereof. Compounds of the formula (I) and (XI) Fare useful as anti-angiogenesis agents and as agents for modulating and/or inhibiting the activity of protein kinases, thus providing treatments for cancer or other diseases associated with cellular proliferation mediated by protein kinases.

INHIBITORS OF VEGF RECEPTOR AND HGF RECEPTOR SIGNALING

The invention relates to the inhibition of vascular endothelial growth factor (VEGF) receptor signaling and hepatocyte growth factor (HGF) receptor signaling. The invention provides compounds and methods for inhibiting VEGF receptor signaling and HGF receptor signaling. The invention also provides compositions and methods for treating cell proliferative diseases and conditions

Development of a scalable synthesis to VEGFR inhibitor AG-28262

The synthesis of N,2-dimethyl-6-(2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2- b]pyridin-7-yloxy)benzo[b]thiophene-3-carboxamide (1, AG-28262) on kilogram scale is described. Initial syntheses of key components 2 and 3 worked well on laboratory scale but had significant drawbacks for larger-scale manufacture. Therefore, new routes to these two key fragments were developed and demonstrated to synthesize kilogram quantities. Key steps involve a two-step thiophenol alkylation/cyclization protocol to synthesize 2 in a convergent manner. A difficult Pd-mediated coupling to produce 3 was replaced with a more scalable stepwise imidazole synthesis. Key rationale for the new routes are discussed.

Thiophene derivatives useful as anticancer agents

The invention relates to compounds of the formula 1 and to pharmaceutically acceptable salts and hydrates thereof, wherein X, Y, R1, R2 and R11 are as defined herein. The invention also relates to pharmaceutical compositions containing the compounds of formula 1 and to methods of treating hyperproliferative disorders in a mammal by administering the compounds of formula 1.