14205-43-7

Basic information

• Product Name: 3-Amino-2-butenoic acid tert-butyl ester
• Synonyms: 3-Amino-2-butenoic acid tert-butyl ester;FINECHEMIE FCHEM13886(WXG00209);FINECHEMIE FCHEM13886
• CAS NO: 14205-43-7
• Molecular Formula: C₈H₁₅NO₂
• Molecular Weight: 157.21
• Mol File: 14205-43-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 37-39 °C(Solv: hexane (110-54-3))
• Boiling Point: 60 °C(Press: 0.4 Torr)
• Appearance: /
• Density: 0.975±0.06 g/cm3(Predicted)
• PKA: 5.32±0.70(Predicted)
• CAS DataBase Reference: 3-Amino-2-butenoic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-2-butenoic acid tert-butyl ester(14205-43-7)
• EPA Substance Registry System: 3-Amino-2-butenoic acid tert-butyl ester(14205-43-7)

Safety Data

• Hazardous Substances Data: 14205-43-7(Hazardous Substances Data)

Upstream product

• 1694-31-1 tert-butyl acetoacetate 

Downstream Products

• 77362-59-5 3-Amino-2-phenylazo-2-butensaeure-tert-butylester 
• 78727-35-2 3-Amino-2-(2,4,6-trimethylphenylazo)-2-butensaeure-tert-butylester 
• 145220-81-1 tert-butyl 2-dimethoxymethyl-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate 
• 102098-34-0 2,6-Dimethyl-4-(2-nitro-phenyl)-5-(2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-1,4-dihydro-pyridine-3-carboxylic acid tert-butyl ester 
• 123754-01-8 2-Imidazol-1-ylmethyl-6-methyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 5-tert-butyl ester 3-ethyl ester 
• 682742-72-9 (2'S)-4-(2'-benzyloxycarbonyl-2'-tert-butoxycarbonylamino-ethyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid di-tert-butyl ester 
• 682742-82-1 (2'S)-4-(2'-amino-2'-benzyloxycarbonyl-ethyl)-2,6-dimethyl-pyridine-3,5-dicarboxylic acid di-tert-butyl ester 
• 596828-16-9 (2'S)-4-(2'-tert-butoxycarbonylamino-2'-carboxyethyl)-2,6-dimethylpyridine-3,5-dicarboxylic acid di-tert-butyl ester 
• 682742-83-2 (2'S)-4-(2'-amino-2'-benzyloxycarbonyl-ethyl)-2,6-dimethyl-1-oxido-pyridine-3,5-dicarboxylic acid di-tert-butyl ester 
• 682742-77-4 (2'S)-4-(2'-benzyloxycarbonyl-2'-tert-butoxycarbonylamino-ethyl)-2,6-dimethyl-pyridine-3,5-dicarboxylic acid di-tert-butyl ester 
• 682742-79-6 (2'S)-4-(2'-benzyloxycarbonyl-2'-tert-butoxycarbonylamino-ethyl)-2,6-dimethyl-1-oxido-pyridine-3,5-dicarboxylic acid di-tert-butyl ester 
• 596828-27-2 (2'S,1''S)-4-[2'-tert-butoxycarbonylamino-2'-(1''-methoxycarbonyl-2''phenylethylcarbamoyl)ethyl]-2,6-dimethylpyridine-3,5-dicarboxylic acid di-tert-butyl ester 
• 682743-08-4 (2'S,1''S)-4-[2'-tert-butoxycarbonylamino-2'-(1''-methoxycarbonyl-2''-phenylethylcarbamoyl)-ethyl]-2,6-dimethyl-1-oxido-pyridine-3,5-dicarboxylic acid di-tert-butyl ester 

Relevant articles and documents

A new modification of the Bohlmann-Rahtz pyridine synthesis

A range of highly functionalised pyridines is prepared from enamino esters and alkynones in a single synthetic step by the use of acetic acid or amberlyst 15 ion exchange resin at 50°C.

Unsymmetric dihydropyridines bearing 2-pyridyl methyl carboxylate as modulators of P-glycoprotein; Synthesis and biological evaluation in resistant and non-resistant cancer cells

Multi-drug resistance (MDR) in cancer cells is often associated with overexpression of P-glycoprotein (P-gp or ABCB1 or MDR1); therefore, modulators of this transporter might be helpful in overcoming MDR. In this study, 16 novel unsymmetrical dihydropyridine (DHP) derivatives bearing 2-pyridyl methyl carboxylate at C3 and a nitroimidazole or nitrophenyl ring at C4 positions of the DHP ring were synthesized. Their cytotoxicity was tested against four human cancer cells by MTT assay. The reversal capacity of MDR was examined in P-gp overexpressing cells (MES-SA/DX5) by measuring the alteration of doxorubicin's IC50 and performing flow cytometric determination of intracellular rhodamine 123 accumulation. The calcium channel blocking (CCB) activity, as a side effect of DHPs, was tested on the ileum of a guinea pig. Molecular docking was performed to explain the binding mode of compounds. Two derivatives, 4a and 4c, containing 4-nitrophenyl at C4 and possessing methyl (4a) and iso-propyl (4c) carboxylates at the C5 position of DHP core demonstrated superior cytotoxic and MDR reversal activities and lower CCB effect. Docking analysis confirmed the importance of the 4-nitrophenyl ring for P-gp inhibitory activity. Some of the synthesized DHP derivatives with considerable MDR reversal capacity could be promising compounds for further discovery of useful agents for management of drug resistant cancer.

Discovery and structure-activity relationships of pyrrolone antimalarials

In the pursuit of new antimalarial leads, a phenotypic screening of various commercially sourced compound libraries was undertaken by the World Health Organisation Programme for Research and Training in Tropical Diseases (WHO-TDR). We report here the detailed characterization of one of the hits from this process, TDR32750 (8a), which showed potent activity against Plasmodium falciparum K1 (EC50 ～ 9 nM), good selectivity (>2000-fold) compared to a mammalian cell line (L6), and significant activity against a rodent model of malaria when administered intraperitoneally. Structure-activity relationship studies have indicated ways in which the molecule could be optimized. This compound represents an exciting start point for a drug discovery program for the development of a novel antimalarial.