149010-53-7

Upstream product

• 50-01-1 guanidine hydrochloride 
• 151864-82-3 Ethyl 4-(4-hydroxy-3-oxobutyl)benzoate 
• 109-77-3 malononitrile 
• 151864-81-2 ethyl 4-(3-oxopropyl)benzoate 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 134373-01-6 4-(4,4-Dicyano-3-dimethoxymethyl-butyl)-benzoic acid tert-butyl ester 
• 151864-73-2 Ethyl 4-<2-(2,4-diaminopyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoate 
• 134373-06-1 4-[4,4-Dimethoxy-3-(2,4,6-triamino-pyrimidin-5-yl)-butyl]-benzoic acid tert-butyl ester 

Downstream Products

• 134373-07-2 Diethyl N-<4-<2-(2,4-diaminopyrrolo<2,3-d>pyrimidin-5-yl)ethyl>benzoyl>-L-glutamate 
• 149010-11-7 (S)-2-{4-[2-(2,4-Diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-4-(3-hydroxy-phenylcarbamoyl)-butyric acid methyl ester 
• 149010-12-8 (S)-2-{4-[2-(2,4-Diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-4-(4-hydroxy-phenylcarbamoyl)-butyric acid methyl ester 
• 181622-87-7 (S)-2-{4-[2-(2,4-Diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-4-(2-hydroxy-phenylcarbamoyl)-butyric acid methyl ester 
• 149010-20-8 (S)-2-{4-[2-(2,4-Diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-4-(1H-tetrazol-5-ylcarbamoyl)-butyric acid methyl ester 
• 149010-16-2 (S)-4-(3-Cyano-phenylcarbamoyl)-2-{4-[2-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-butyric acid methyl ester 
• 149010-17-3 (S)-4-(4-Cyano-phenylcarbamoyl)-2-{4-[2-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-butyric acid methyl ester 
• 181622-85-5 (S)-4-(2-Cyano-phenylcarbamoyl)-2-{4-[2-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-butyric acid methyl ester 
• 149010-15-1 2-((S)-4-{4-[2-(2,4-Diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-4-methoxycarbonyl-butyrylamino)-benzoic acid methyl ester 
• 149010-09-3 3-((S)-4-{4-[2-(2,4-Diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-4-methoxycarbonyl-butyrylamino)-benzoic acid ethyl ester 
• 149010-19-5 (S)-2-{4-[2-(2,4-Diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-4-(3-methoxycarbonylmethyl-phenylcarbamoyl)-butyric acid methyl ester 
• 149010-10-6 4-((S)-4-{4-[2-(2,4-Diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-4-methoxycarbonyl-butyrylamino)-benzoic acid ethyl ester 
• 181622-99-1 6-((S)-4-{4-[2-(2,4-Diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-4-methoxycarbonyl-butyrylamino)-nicotinic acid methyl ester 
• 181622-86-6 (S)-2-{4-[2-(2,4-Diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-ethyl]-benzoylamino}-4-[2-(1H-tetrazol-5-yl)-phenylcarbamoyl]-butyric acid methyl ester 

Relevant academic research and scientific papers

Analogues of 4-[(7-Bromo-2-methyl-4-oxo-3 H -quinazolin-6-yl)methylprop-2- ynylamino]- N -(3-pyridylmethyl)benzamide (CB-30865) as potent inhibitors of nicotinamide phosphoribosyltransferase (Nampt)

We have shown previously that the target of the potent cytotoxic agent 4-[(7-bromo-2-methyl-4-oxo-3H-quinazolin-6-yl)methyl-prop-2-ynylamino] -N-(3-pyridylmethyl)benzamide (CB38065, 1) is nicotinamide phosphoribosyltransferase (Nampt). With its cellular target known we sought to optimize the biochemical and cellular Nampt activity of 1 as well as its cytotoxicity. It was found that a 3-pyridylmethylamide substituent in the A region was critical to cellular Nampt activity and cytotoxicity, although other aromatic substitution did yield compounds with submicromolar enzymatic inhibition. Small unsaturated groups worked best in the D-region of the molecule, with 3,3-dimethylallyl providing optimal potency. The E region required a quinazolin-4-one or 1,2,3-benzotriazin-4-one group for activity, and many substituents were tolerated at C2 of the quinazolin-4-one. The best compounds showed subnanomolar inhibition of Nampt and low nanomolar cytotoxicity in cellular assays.

NEW CLASSICAL ANTIFOLATES

The present invention is directed to antifolate compounds having the structure of formula (I). wherein: X is CHR9 or NR9; Y1, Y2, and Y3 independently are O or S; V1 and V2 independently are O, S, or NZ; Z is H, optionally substituted alkyl, optionally su

A one-step ring transformation/ring annulation approach to pyrrolo[2,3-d]pyrimidines. A new synthesis of the potent DHFR inhibitor TNP-351

Condensation of amidines with 2-amino-3-cyanofurans gives 2-substituted-4-aminopyrrolo[2,3-d]pyrimidines by a ring-opening, ring-recyclization sequence of reactions through which the starting furan 2-amino nitrogen becomes the pyrrole nitrogen of the final product and one of the amidine nitrogens becomes N-1 of the fused pyrimidine ring. 2,4-Diamino-5-[2-(4-carbethoxyphenyl)ethyl]pyrrolo[2,3-d]pyrimidine, a key intermediate in the synthesis of the DHFR inhibitor TNP-351, has been prepared in one step by reaction of ethyl 4-[2-(2-amino-3-cyanofuran-4-yl)ethyl]benzoate with guanidine.

A Novel Synthetic Approach to Pyrrolopyrimidine Antifolates

A novel and efficient synthetic method for the synthesis of pyrrolopyrimidine antifolates is described.The key reaction of this method is the photo-initiated free radical addition of bromomalononitrile or ethyl bromocyanoacetate to an enol ether to afford the backbone skeleton of the targeted antifolate molecule.The key intermediates 3 or 4 are smoothly converted to the pyrrolopyrimidine antifolates 1 or 2 in three steps and in high overall yield.