149765-16-2

Basic information

• Product Name: Propanamide, N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-
• Synonyms: N-(4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyriMidin-2-yl)-2,2-diMethyl propanaMide;N-(4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyriMidin-2-yl)pivalaMide;4-chloro-5-iodo-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidine;Propanamide, N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-;N-(4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropionamide;N2-Pivaloyl-4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyriMidine
• CAS NO: 149765-16-2
• Molecular Formula: C₁₁H₁₂ClIN₄O
• Molecular Weight: 378.6
• Mol File: 149765-16-2.mol
• Article Data: 11

Chemical Properties

• Melting Point: 240 °C(Solv: methanol (67-56-1))
• Appearance: /
• Density: 1.847g/cm³
• Refractive Index: 1.716
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 5.97±0.40(Predicted)
• CAS DataBase Reference: Propanamide, N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Propanamide, N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-(149765-16-2)
• EPA Substance Registry System: Propanamide, N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-(149765-16-2)

Safety Data

• Hazardous Substances Data: 149765-16-2(Hazardous Substances Data)

Usage

General Description

Propanamide, N-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl- is a chemical compound with the molecular formula C13H14ClIN4O. It is a derivative of pyrrolopyrimidine, a heterocyclic compound that has been investigated for its potential pharmaceutical properties. This specific compound contains a propanamide group and two methyl substituents, along with a chloro and iodo atom attached to the pyrrolopyrimidine ring. The compound may have potential applications in the field of medicinal chemistry and drug development, although further research is needed to fully understand its biological activity and potential uses.

InChI:InChI=1/C11H12ClIN4O/c1-11(2,3)9(18)17-10-15-7(12)6-5(13)4-14-8(6)16-10/h4H,1-3H3,(H2,14,15,16,17,18)

Upstream product

• 7355-55-7 2-amino-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 
• 3282-30-2 pivaloyl chloride 
• 137281-08-4 N-(4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)pivalamide 
• 84955-31-7 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine 
• 149765-15-1 N-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl-propionamide 

Downstream Products

• 199938-73-3 chloro-7-[2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythro-pentofuranosyl]-5-iodo-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidine 
• 933995-43-8 4-chloro-5-iodo-2-pivalamido-7-(2,3,5-tri-O-benzoyl-β-L-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1394818-93-9 C₁₈H₁₈ClIN₄O 
• 848698-31-7 C₂₁H₂₀ClN₅O 
• 873792-67-7 4-chloro-5-iodo-2-(pivaloylamino)-7-[(2,3,5-tri-O-benzoyl)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 798574-62-6 4-chloro-7-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-5-iodo-2-pivaloylamino-7H-pyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

Synthesis of Galactosyl-Queuosine and Distribution of Hypermodified Q-Nucleosides in Mouse Tissues

Queuosine (Q) is a hypermodified RNA nucleoside that is found in tRNAHis, tRNAAsn, tRNATyr, and tRNAAsp. It is located at the wobble position of the tRNA anticodon loop, where it can interact with U as well as C bases located at the respective position of the corresponding mRNA codons. In tRNATyr and tRNAAsp of higher eukaryotes, including humans, the Q base is for yet unknown reasons further modified by the addition of a galactose and a mannose sugar, respectively. The reason for this additional modification, and how the sugar modification is orchestrated with Q formation and insertion, is unknown. Here, we report a total synthesis of the hypermodified nucleoside galactosyl-queuosine (galQ). The availability of the compound enabled us to study the absolute levels of the Q-family nucleosides in six different organs of newborn and adult mice, and also in human cytosolic tRNA. Our synthesis now paves the way to a more detailed analysis of the biological function of the Q-nucleoside family.

EC144 is a potent inhibitor of the heat shock protein 90

Alkyne 40, 5-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl) methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylpent-4-yn-2-ol (EC144), is a second generation inhibitor of heat shock protein 90 (Hsp90) and is substantially more potent in vitro and in vivo than the first generation inhibitor 14 (BIIB021) that completed phase II clinical trials. Alkyne 40 is more potent than 14 in an Hsp90α binding assay (IC50 = 1.1 vs 5.1 nM) as well as in its ability to degrade Her-2 in MCF-7 cells (EC 50 = 14 vs 38 nM). In a mouse model of gastric tumors (N87), 40 stops tumor growth at 5 mg/kg and causes partial tumor regressions at 10 mg/kg (po, qd× 5). Under the same conditions, 14 stops tumor growth only at 120 mg/kg, and does not induce partial regressions. Thus, alkyne 40 is approximately 20-fold more efficacious than 14 in mice.

Synthesis of the transfer-RNA nucleoside queuosine by using a chiral allyl azide intermediate

Chilled out: Chiral allyl azides are rarely used in natural product synthesis because of their tendency to undergo a [3.3] sigmatropic rearrangement (see scheme, top). In allylic cyclopentenyl azides, this rearrangement can be suppressed at just 0°C, enabling a short convergent synthesis of the hypermodified transfer-RNA nucleoside queuosine. (Chemical Equation Presented).