123148-78-7

Usage

Uses

6-Chloro-7-iodo-7-deazapurine is used as pharmaceutical intermediate.

InChI:InChI=1/C6H3ClIN3/c7-5-4-3(8)1-9-6(4)11-2-10-5/h1-2H,(H,9,10,11)

Upstream product

• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 3680-71-5 1H-pyrrolo[2,3-d]pyrimidin-4(7H)-one 
• 52133-67-2 ethyl 2-cyano-4,4-diethoxybutyrate 
• 1615680-91-5 6-chloro-5-((trimethylsilyl)ethynyl)pyrimidin-4-amine 
• 3680-71-5 7-deazahypoxanthine 
• 3680-71-5 Allopurinol 
• 162101-31-7 (2-fluoro-4-methoxyphenyl)boronic acid 
• 1207543-30-3 4‐chloro‐5‐iodo‐7‐((2‐(trimethylsilyl)ethoxy)methyl)‐7H‐pyrrolo[2,3‐d]pyrimidine 
• 67831-84-9 2-thioxo-1,2,3,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 7400-05-7 6-amino-5-(2,2-diethoxyethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one 
• 516-12-1 N-iodo-succinimide 

Downstream Products

• 123148-82-3 7-(2-Benzyloxy-1-benzyloxymethyl-ethoxymethyl)-4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine 
• 178420-94-5 (2R,3S,5R)-5-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate 
• 908130-61-0 β-L-2'-deoxy-7-iodotubercidin 
• 85209-84-3 5'-deoxy-5-iodotubercidin 
• 867164-06-5 4-chloro-5-iodo-7-phenyl-7H-pyrrolo[2,3-d]pyrimidine 
• 862729-11-1 4-chloro-5-iodo-7-(3,4,5-trimethoxy-benzyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 213744-81-1 4-chloro-5-iodo-7-isopropyl-7H-pyrrolo[2,3-d]pyrimidine 
• 911122-72-0 7-but-3-enyl-4-chloro-5-iodopyrrolo[2,3-d]pyrimidine 
• 934815-82-4 C₃₄H₂₉ClIN₃O₃ 
• 208459-84-1 7-Benzenesulfonyl-4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine 
• 1082951-06-1 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbut-3-yn-2-ol 
• 847551-25-1 4-chloro-5-iodo-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 862729-09-7 4-chloro-5-iodo-7-(4-nitro-benzyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1228504-15-1 4-chloro-5-iodo-7-m-tolyl-7H-pyrrolo[2,3-d]pyrimidine 

Relevant academic research and scientific papers

Study on the synthesis and PKA-I binding activities of 5-alkynyl tubercidin analogues

5-Alkynyl tubercidin analogues were synthesized and their biologica activities were evaluated. It was found that protein kinase A could be activated by 5-alkynyl tubercidin (9a) and cAMP- binding ability to PKA-I was selectively inhibited by it. Molecular

Identification of fused pyrimidines as interleukin 17 secretion inhibitors

Inhibiting the interleukin 17 pathway is of interest in a number of autoimmune diseases. Herein, 42 fused pyrimidines have been evaluated as interleukin 17 secretion inhibitors using a phenotypic assay with peripheral blood mononuclear cells. 7H-Pyrrolo [

Synthesis of responsive fluorescent nucleobases 7-(benzofuran-2-yl)-7-deazahypoxanthine and 7-(benzofuran-2-yl)-7-deazaguanine using cross-coupling reaction

In order to develop fluorescent guanine analogs having substitutions at the 7-positions, 7-(benzofuran-2-yl)-7-deaza-hypoxanthine (1a) and 7-(benzofuran-2-yl)-7-deazaguanine (1b), were synthesized from 7-deaza-7-iodohypoxanthine and 7-deaza-7-iodo-2-N-pivaloylguanine via a Suzuki-Miyaura cross-coupling, respectively. Compound 1b showed strong fluorescence, with higher fluorescent quantum yields in less polar solvents; meanwhile, 1a showed higher activity in more polar solvents. It is expected that the guanine analogs can be incorporated into nucleosides to develop new fluorescent oligonucleotides.

Pre-steady state kinetic analysis of cyclobutyl derivatives of 2′-deoxyadenosine 5′-triphosphate as inhibitors of HIV-1 reverse transcriptase

Pre-steady state kinetic analysis was utilized for biochemical evaluation of a series of cyclobutyl adenosine nucleotide analogs with HIV-1 RT WT. The phosphonyl-diphosphate form of the cyclobutyl nucleotide, 5, was the most efficiently incorporated of the series. Nucleotide 5 was fourfold more efficiently incorporated than the FDA approved TFV-DP by RTWT. The kinetics of incorporation for 5 using the drug resistant mutant enzyme K65R was also determined. Compound 5 was threefold more efficiently incorporated compared to TFV-DP with RTK65R. These results demonstrate cyclobutyl adenosine analogs can act as substrates for incorporation by HIV-1 RT and be a potential scaffold for HIV inhibitors.

Potent and selective EGFR inhibitors based on 5-aryl-7H-pyrrolopyrimidin-4-amines

The epidermal growth factor receptor represents an important target in cancer therapy, and low molecular weight inhibitors based on quinazolines have reached the marked. Herein we report on a new scaffold, 5-aryl-7H-pyrrolo[2,3-d]pyrimidin-4-amines, and show that when employing (S)-phenylglycinol as C-4 substituent, potent inhibitors can be made. The two most active inhibitors have suitable druglike properties, were equipotent with Erlotinib in Ba/F3 cell studies, and showed lower cross reactivity than Erlotinib in a panel of 50 kinases.

Inhibition of osimertinib-resistant epidermal growth factor receptor EGFR-T790M/C797S

Precision medicine has revolutionized the treatment of patients in EGFR driven non-small cell lung cancer (NSCLC). Targeted drugs show high response rates in genetically defined subsets of cancer patients and markedly increase their progression-free survival as compared to conventional chemotherapy. However, recurrent acquired drug resistance limits the success of targeted drugs in long-term treatment and requires the constant development of novel efficient inhibitors of drug resistant cancer subtypes. Herein, we present covalent inhibitors of the drug resistant gatekeeper mutant EGFR-L858R/T790M based on the pyrrolopyrimidine scaffold. Biochemical and cellular characterization, as well as kinase selectivity profiling and western blot analysis, substantiate our approach. Moreover, the developed compounds possess high activity against multi drug resistant EGFR-L858R/T790M/C797S in biochemical assays due to their highly reversible binding character, that was revealed by characterization of the binding kinetics. In addition, we present the first X-ray crystal structures of covalent inhibitors in complex with C797S-mutated EGFR which provide detailed insight into their binding mode.

Synthesis and photophysical evaluation of new fluorescent 7-arylethynyl-7-deazaadenosine analogs

Three new fluorescent 7-deaza-2′-deoxyadenosine analogs were synthesized via the Sonogashira cross-coupling reaction of 7-iodo-7-deaza-2′-deoxyadenosine with 1-ethynylpyrene, 2-ethynyl-6-methoxynaphthalene, and 9-ethynylphenanthrene. The spectral properties of these analogs were evaluated in dioxane, EtOH, and H2O to determine their potential for use as environmentally sensitive fluorescent probes. All three analogs displayed large solvatofluorochromicity in H2O, relative to their emission wavelengths in dioxane or EtOH. Moreover, all three analogs exhibited microenvironmental sensitivity of their fluorescence emission intensity, being moderate to high quantum yields in dioxane and EtOH and significantly lower in H2O. Various attempts to perform domino cross-coupling and annuation reactions on 7-deaza-7-alkynyladenine derivatives to form a new fused tricyclic adenine analog were unsuccessful.

Inhibitors of NEK7 kinase

Compounds having activity as inhibitors of NEK7 are provided. The compounds have Structure (I):or a pharmaceutically acceptable salt, stereoisomer or prodrug thereof, wherein, A, X, Y, R1, R2, R3, R4 and R5 are as defined herein. Methods associated with p

Selective C-H Iodination of (Hetero)arenes

Iodoarenes are versatile intermediates and common synthetic targets in organic synthesis. Here, we present a strategy for selective C-H iodination of (hetero)arenes with a broad functional group tolerance. We demonstrate the utility and differentiation to other iodination methods of supposed sulfonyl hypoiodites for a set of carboarenes and heteroarenes.

Novel HPK1 inhibitor as well as preparation method and application thereof

The present invention provides an HPK1 kinase inhibitor, the preparation thereof and use thereof. Specifically, the present invention provides a compound as represented by formula I. The definitions on groups are as stated in the description. The compound has excellent HPK1 inhibitory activity, and therefore can be used for preparing a pharmaceutical composition for treating cancer and other diseases related to HPK1 activity.