468068-39-5

Usage

Properties

1. Chemical Formula: $C6H5ClN4O$
2. Derivative: Derived from pyridinecarboximidamide
3. Functional Groups:
Chlorine atom (Cl)
Hydroxyl group (OH)
4. Potential Applications:
Medicinal chemistry
Pharmaceutical drug development
5. Unique Structure:
Presence of chlorine atom and hydroxyl group attached to the pyridine ring
6. Promise for Further Research:
Promising candidate for synthesis of novel compounds with potential therapeutic properties
7. Utility:
Useful in various chemical and biochemical processes in laboratory or industrial settings

Structure

Contains a chlorine atom and a hydroxyl group attached to the pyridine ring

Applications

Medicinal chemistry: Potential use in drug discovery and development
Pharmaceutical drug development: May serve as a precursor or intermediate in the synthesis of pharmaceuticals

Potential

Promising candidate for further research due to its unique structure and functional groups

Utility

Useful in various chemical and biochemical processes, both in laboratory and industrial settings, owing to its chemical properties and reactivity

Upstream product

• 33252-28-7 6-chloronicotinonitrile 

Downstream Products

• 1201594-74-2 4-[3-(6-chloropyridin-3-yl)-1,2,4-oxadiazol-5-yl]benzonitrile 

Relevant academic research and scientific papers

Discovery and development of a novel N-(3-bromophenyl)-{[(phenylcarbamoyl)amino]methyl}-N-hydroxythiophene-2-carboximidamide indoleamine 2,3-dioxygenase inhibitor using knowledge-based drug design

Indoleamine 2,3-dioxygenase-1 (IDO1) is a potential target for the next generation of cancer immunotherapies. We describe the development of two series of IDO1 inhibitors incorporating a N-hydroxy-thiophene-carboximidamide core generated by knowledge-based drug design. Structural modifications to improve the cellular activity and pharmacokinetic (PK) properties of the compounds synthesized, including extension of the side chain of the N-hydroxythiophene-2-carboximidamide core, resulted in compound 27a, a potent IDO1 inhibitor which demonstrated significant (51%) in vivo target inhibition on IDO1 in a human SK-OV-3 ovarian xenograft tumor mouse model. This strategy is expected to be applicable to the discovery of additional IDO1 inhibitors for the treatment of other diseases susceptible to modulation of IDO1.

NOVEL 1,2,4 OXADIAZOLE COMPOUNDS AND METHODS OF USE THEREOF

The invention relates to 1,2,4 oxadiazole compounds and analogs thereof, represented by formula (II), and compositions and methods of use thereof.

PHARMACEUTICAL COMPOSITIONS AND THEIR METHODS OF USE

The invention relates to a composition comprising a neuronal nicotinic receptor ligand and an α4β2 positive allosteric modulator, a method of using the same, and a related article of manufacture.

CYCLOALKYLAMINO ACID DERIVATIVES

The invention relates to compounds of formula I and to pharmaceutically acceptable salts, prodrugs, solvates or hydrates thereof; wherein B, D, E, R1, R2, R3, R4, R5, R8, m, n, p, q, r, s, t and u are as defined herein. This invention also relates to a method of using such compounds in the treatment of hyperproliferative diseases and autoimmune diseases in mammals, especially humans, and to pharmaceutical compositions containing such compounds.

Discovery and structure-activity relationship of 3-aryl-5-aryl-1,2,4- oxadiazoles as a new series of apoptosis inducers and potential anticancer agents

We have identified 5-(3-chlorothiophen-2-yl)-3-(4-trifluoromethylphenyl)-1, 2,4-oxadiazole (1d) as a novel apoptosis inducer through our caspase- and cell-based high-throughput screening assay. Compound 1d has good activity against several breast and colorectal cancer cell lines but is inactive against several other cancer cell lines. In a flow cytometry assay, treatment of T47D cells with 1d resulted in arrest of cells in the G1 phase, followed by induction of apoptosis. SAR studies of Id showed that the 3-phenyl group can be replaced by a pyridyl group, and a substituted five-member ring in the 5-position is important for activity. 5-(3-Chlorothiophen-2-yl)-3-(5- chloropyridin-2-yl)-1,2,4-oxadiazole (41) has been found to have in vivo activity in a MX-1 tumor model. Using a photoaffinity agent, the molecular target has been identified as TIP47, an IGFII receptor binding protein. Therefore, our cell-based chemical genetics approach for the discovery of apoptosis inducers can identify potential anticancer agents as well as their molecular targets.

Synthesis and Antiprotozoal Activity of Aza-Analogues of Furamidine

6-[5-(4-Amidinophenyl)furan-2-yl]nicotinamidine (8a) was synthesized from 6-[5-(4-cyanophenyl)furan-2-yl]nicotinonitrile (4a), through the bis-O-acetoxyamidoxime followed by hydrogenation. Compound 4a was prepared via selective bromination of 6-(furan-2-yl)nicotinonitrile (2a) with N-bromosuccinimide, followed by Suzuki coupling with 4-cyanophenylboronic acid. In a similar way, diamidines 8b and 8c were prepared from the dicyano derivatives 4c and 4d, respectively. N-Methoxy-6-[5-[4-(N-methoxyamidino)phenyl]-furan-2-yl}-nicotinamidine (6a) was prepared via methylation of the respective diamidoxime 5a with dimethylsulfate. Prodrugs 6b and 6c were also prepared by methylation of the respective diamidoximes 5b and 5d. The symmetrical diamidines 14a,b were synthesized through the corresponding bis-O-acetoxyamidoxime followed by hydrogenation. The key compounds 11a,b were conveniently obtained by Stille coupling between 2,5-bis(tri-n-butylstannyl)furan and the corresponding heteroaryl halides. These compounds have been evaluated in vitro for activity against Trypanosoma b. rhodesiense (T. b. r.) and P. falciparum (P. f.). The diamidines 8a, 8c, and 14b gave IC50 values versus T. b. r. of less than 10 nM. Against P. f. 8a, 8b, and 14b exhibited IC50 values less than 10 nM. In an in vivo mouse model for T. b. r. four compounds 6a, 6c, 6d, and 8a were curative. Compound 6a produced cures at an oral dosage of 5 mg/kg.

Substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs as activators of caspases and inducers of apoptosis and the use thereof

The present invention is directed to substituted 3-aryl-5-aryl-[1,2,4]-oxadiazoles and analogs thereof, represented by the Formula I: wherein Ar1, Ar3, A, B and D are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.