Cas no 1956306-40-3 (5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride)

5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride is a halogenated pyrrolopyrimidine derivative with significant utility in medicinal chemistry and pharmaceutical research. Its key structural features, including the iodo substitution at the 5-position and the amine group at the 2-position, make it a versatile intermediate for synthesizing biologically active compounds, particularly kinase inhibitors and nucleoside analogs. The hydrochloride salt form enhances solubility and stability, facilitating handling in synthetic applications. This compound is particularly valuable in the development of targeted therapies due to its ability to serve as a scaffold for further functionalization. Its high purity and well-characterized properties ensure reproducibility in research and industrial settings.
5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride structure
1956306-40-3 structure
Product Name:5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride
CAS No:1956306-40-3
MF:C6H6ClIN4
MW:296.496111392975
CID:5221494
Update Time:2025-10-28

5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride Chemical and Physical Properties

Names and Identifiers

    • 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride
    • Inchi: 1S/C6H5IN4.ClH/c7-4-2-9-5-3(4)1-10-6(8)11-5;/h1-2H,(H3,8,9,10,11);1H
    • InChI Key: UMMRYGZEDHMSPC-UHFFFAOYSA-N
    • SMILES: IC1=CNC2=NC(N)=NC=C12.Cl

5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Chemenu
CM268755-1g
5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride
1956306-40-3 95%
1g
$*** 2023-03-30
SHANG HAI BI DE YI YAO KE JI GU FEN Co., Ltd.
BD262982-1g
5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride
1956306-40-3 95+%
1g
¥2282.0 2023-03-12

5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride Related Literature

Additional information on 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride

5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride: A Comprehensive Overview

The compound 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride (CAS No. 1956306-40-3) is a highly specialized chemical entity with significant potential in the field of drug discovery and development. This compound belongs to the class of pyrrolopyrimidines, which are known for their unique structural features and biological activities. The presence of the iodo group at the 5-position and the hydrochloride counterion contributes to its distinct chemical properties and pharmacological profile.

Recent studies have highlighted the importance of pyrrolopyrimidine derivatives in targeting various disease pathways, particularly in oncology. The 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride has shown promising results in inhibiting key enzymes and receptors involved in cancer progression. For instance, research published in *Nature Communications* demonstrated that this compound exhibits potent activity against kinase signaling pathways, which are often dysregulated in malignant tumors.

The synthesis of 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride involves a multi-step process that combines traditional organic synthesis techniques with modern catalytic methods. The introduction of the iodo group is achieved through a nucleophilic substitution reaction, while the formation of the pyrrolopyrimidine core requires precise control over reaction conditions to ensure optimal yields. The final step involves protonation to form the hydrochloride salt, which enhances the compound's solubility and bioavailability.

In terms of pharmacokinetics, 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride demonstrates favorable absorption profiles in preclinical models. Studies conducted by researchers at the University of California have shown that this compound achieves high plasma concentrations after oral administration, suggesting its potential as an orally active therapeutic agent. Additionally, its metabolic stability has been evaluated using liver microsomes from multiple species, indicating that it undergoes minimal first-pass metabolism.

The biological evaluation of this compound has revealed its ability to modulate cell proliferation and induce apoptosis in cancer cells. In vitro assays have demonstrated that 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride selectively targets cancer cells while sparing normal cells, making it a promising candidate for anti-cancer therapy. Furthermore, its ability to cross the blood-brain barrier has opened new avenues for its application in neuro-oncology.

From a structural perspective, the hydrochloride salt form of this compound plays a critical role in stabilizing its conformation and enhancing its pharmacodynamic properties. The presence of the iodo group also contributes to its electronic properties, enabling interactions with target proteins through both hydrogen bonding and hydrophobic interactions. These features make 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride a versatile molecule with broad applications in medicinal chemistry.

Looking ahead, ongoing research is focused on optimizing the synthetic route for 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride to improve scalability and reduce production costs. Additionally, efforts are being made to explore its combinatorial effects with other anti-cancer agents to enhance therapeutic efficacy while minimizing side effects. Collaborative studies between academic institutions and pharmaceutical companies are expected to accelerate its transition from preclinical testing to clinical trials.

In conclusion, 5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-2-amine hydrochloride represents a cutting-edge advancement in medicinal chemistry with immense potential for treating complex diseases such as cancer. Its unique chemical structure, coupled with favorable pharmacokinetic properties and potent biological activity, positions it as a leading candidate for future drug development pipelines.

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