(2S,5R)-5-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydro-2-furanmethanol
[CAS# 114748-70-8]

Identification

• Classification: API >> Antineoplastic agents >> Antimetabolite antineoplastic
• Name: (2S,5R)-5-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydro-2-furanmethanol
• Synonyms: 7-Iodo-2',3'-dideoxy-7-deazaadenosine
• Protein Sequence: N
• Molecular Formula: C₁₁H₁₃IN₄O₂
• Molecular Weight: 360.15
• CAS Registry Number: 114748-70-8
• SMILES: C1C[C@@H](O[C@@H]1CO)N2C=C(C3=C(N=CN=C32)N)I

Properties

• Solubility: Very slightly soluble (0.68 g/L) (25 ºC), Calc.^*
• Density: 2.21±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.847, Calc.^*
• Boiling Point: 579.3±50.0 ºC (760 mmHg), Calc.^*
• Flash Point: 304.2±30.1 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319
• Precautionary Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovory and Applicatios

The chemical substance (2S,5R)-5-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydro-2-furanmethanol is an organic compound that belongs to the class of pyrrolo[2,3-d]pyrimidine derivatives, which are notable for their biological activity, especially in the realm of medicinal chemistry. The compound contains both a tetrahydrofuran (THF) ring and a pyrrolo[2,3-d]pyrimidine moiety, contributing to its structural complexity.

The compound is a chiral molecule, with specific stereochemistry at the 2S and 5R positions, indicating a particular spatial arrangement of its atoms. This stereochemical configuration is crucial for its interaction with biological targets and its potential as a therapeutic agent. The presence of the amino and iodine atoms on the pyrrolo[2,3-d]pyrimidine structure enhances the molecule's reactivity and can influence its binding to biological receptors.

In terms of discovery, (2S,5R)-5-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydro-2-furanmethanol was likely synthesized as part of ongoing research into developing potent biologically active compounds for various therapeutic areas. Pyrrolo[2,3-d]pyrimidine derivatives, including those with modified substituents such as amino and halogen groups, have been studied for their potential in targeting enzymes, receptors, and other biological molecules involved in diseases like cancer, viral infections, and autoimmune disorders.

One significant application of (2S,5R)-5-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydro-2-furanmethanol is in the development of kinase inhibitors. Kinases are enzymes that play a crucial role in various cellular processes, including cell division, growth, and apoptosis. Abnormal kinase activity is often associated with diseases such as cancer and chronic inflammation. Compounds like this one, which are designed to inhibit specific kinases, hold promise for use in targeted therapies for these conditions. The iodine and amino substitutions on the pyrrolo[2,3-d]pyrimidine core may contribute to selective binding to particular kinase targets, thereby enhancing the therapeutic potential of such compounds.

Additionally, the presence of the tetrahydrofuranmethanol group in the structure of the compound may lend itself to interactions with other biological molecules, further expanding its potential application in drug design. This part of the molecule could play a role in facilitating the compound's solubility, stability, or pharmacokinetic properties, which are essential for its development as a drug candidate.

The synthesis of (2S,5R)-5-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydro-2-furanmethanol involves standard organic chemistry techniques such as nucleophilic substitution, coupling reactions, and possibly cyclization steps to form the fused pyrrolo[2,3-d]pyrimidine ring system. The stereochemical purity of the compound would be crucial for its activity, as the specific 2S,5R configuration is likely to influence the way it interacts with biological targets.

Safety and handling of this compound require standard precautions for chemicals of its type. It should be handled with care in a well-ventilated laboratory, and protective equipment such as gloves and goggles should be used to avoid exposure. As the compound contains iodine, which is a hazardous material, it should be stored appropriately to prevent unwanted reactions or exposure.

In summary, (2S,5R)-5-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)tetrahydro-2-furanmethanol is a bioactive compound with potential applications in the development of targeted therapies, particularly as a kinase inhibitor. The compound's complex structure and stereochemistry make it an interesting subject of study in medicinal chemistry, with the possibility of being developed for the treatment of various diseases, especially those associated with abnormal kinase activity.