Production Method 1

800401-67-6

800401-68-7

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  1 h, reflux
1.2 Reagents: Acetic acid Solvents: Water ;  pH 4

Reference

Synthesis of the new ring system bispyrido[4',3':4,5]pyrrolo[1,2-a:1',2'-d]pyrazine and its deaza analogue

Parrino, Barbara; Spano, Virginia; Carbone, Anna; Barraja, Paola; Diana, Patrizia; et al, Molecules, 2014, 19(9), 13342-13357

Production Method 2

800401-67-6

800401-68-7

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Ethanol ,  Water ;  reflux

Reference

Novel Liver-targeted conjugates of Glycogen Phosphorylase Inhibitor PSN-357 for the Treatment of Diabetes: Design, Synthesis, Pharmacokinetic and Pharmacological Evaluations

Zhang, Liying; Song, Chengjun; Miao, Guangxin; Zhao, Lianzhi; Yan, Zhiwei; et al, Scientific Reports, 2017, 7,

5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid Raw materials

• Ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid Preparation Products

• 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (800401-68-7)

• 1. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
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• 2. Excitable dynamics in the bromate–sulfite–ferrocyanide reaction
  J. Zagora,M. Vosla?,L. Schreiberová,I. Schreiber Phys. Chem. Chem. Phys., 2002,4, 1284-1291
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  Analyst, 1996,121, 785-788
• 5. Excimer and exciplex formation in a pair of bright phosphorescent isomers constructed from Cu3(pyrazolate)3 and Cu3I3 coordination luminophores?
  Shun-Ze Zhan,Mian Li,Xiao-Ping Zhou,Dan Li,Seik Weng Ng RSC Adv., 2011,1, 1457-1459

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolopyridines Pyrrolopyridines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolopyridines

5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic Acid (CAS No. 800401-68-7): An Overview of Its Structure, Synthesis, and Applications in Medicinal Chemistry

5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (CAS No. 800401-68-7) is a versatile organic compound that has garnered significant attention in the field of medicinal chemistry due to its unique structural features and potential biological activities. This compound belongs to the class of pyrrolopyridines, which are known for their diverse pharmacological properties, including antiviral, anticancer, and anti-inflammatory activities.

The molecular structure of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid is characterized by a fused pyrrole and pyridine ring system with a chlorine substituent at the 5-position and a carboxylic acid group at the 2-position. The presence of these functional groups imparts distinct chemical reactivity and biological activity to the molecule. The chlorine substituent can influence the electronic properties of the molecule, affecting its binding affinity to various biological targets.

In recent years, significant progress has been made in the synthesis and characterization of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid. One of the most common synthetic routes involves the condensation of 5-chloropyrrole-2-carbaldehyde with malononitrile followed by hydrolysis to form the carboxylic acid. This method is efficient and scalable, making it suitable for both laboratory-scale synthesis and industrial production.

The biological activities of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid have been extensively studied in various in vitro and in vivo models. Research has shown that this compound exhibits potent antiviral activity against several RNA viruses, including influenza and hepatitis C viruses. The mechanism of action is believed to involve the inhibition of viral replication through interference with key viral enzymes or host cell pathways.

Beyond its antiviral properties, 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid has also demonstrated promising anticancer activity. Studies have reported that this compound can induce apoptosis in various cancer cell lines by modulating signaling pathways involved in cell proliferation and survival. For example, it has been shown to inhibit the activation of Akt and ERK signaling pathways, which are frequently dysregulated in cancer cells.

In addition to its direct biological effects, 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid serves as an important building block for the synthesis of more complex molecules with enhanced pharmacological properties. Derivatives of this compound have been synthesized and evaluated for their improved potency and selectivity against specific targets. For instance, N-substituted derivatives have shown enhanced antiviral activity against drug-resistant strains of influenza virus.

The potential applications of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid extend beyond its use as a therapeutic agent. It is also a valuable tool for chemical biology research, enabling scientists to probe the function of specific proteins and pathways in living systems. For example, it can be used as a probe to study the role of specific enzymes in viral replication or cancer cell signaling.

In conclusion, 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (CAS No. 800401-68-7) is a multifaceted compound with significant potential in medicinal chemistry. Its unique structural features and diverse biological activities make it an attractive target for further research and development. As our understanding of its mechanisms of action continues to grow, it is likely that new applications will emerge, contributing to the advancement of drug discovery and therapeutic interventions.

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