528599-00-0

Basic information

• Product Name: Benzoic acid, 2-(2-propynyloxy)-, ethyl ester
• CAS NO: 528599-00-0
• Molecular Formula: C12H12O3
• Molecular Weight: 204.225
• Mol File: 528599-00-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 2-(2-propynyloxy)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2-(2-propynyloxy)-, ethyl ester(528599-00-0)
• EPA Substance Registry System: Benzoic acid, 2-(2-propynyloxy)-, ethyl ester(528599-00-0)

Safety Data

• Hazardous Substances Data: 528599-00-0(Hazardous Substances Data)

Upstream product

• 106-96-7 propargyl bromide 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 6921-27-3 dipropargyl ether 

Downstream Products

• 1042422-99-0 C₁₈H₁₆O₃ 
• 528599-01-1 2-{3-[3-(2,4-diamino-pyrimidin-5-ylmethyl)-4-methoxy-phenyl]-prop-2-ynyloxy}-benzoic acid ethyl ester 
• 528598-99-4 2-{3-[3-(2,4-diamino-pyrimidin-5-ylmethyl)-4-methoxy-phenyl]-prop-2-ynyloxy}-benzoic acid 

Relevant articles and documents

Copper-Catalyzed Ring Opening of [1.1.1]Propellane with Alkynes: Synthesis of Exocyclic Allenic Cyclobutanes

Despite the long history and interesting properties of propellanes, these compounds still have tremendous potential to be exploited in synthetic organic chemistry. Herein we disclose an experimentally simple procedure to achieve cyclobutane-containing allenes and alkynes through a copper-catalyzed ring opening of [1.1.1]propellane and subsequent reaction with ethynes.

Further studies on 2,4-diamino-5-(2′,5′-disubstituted benzyl)pyrimidines as potent and selective inhibitors of dihydrofolate reductases from three major opportunistic pathogens of AIDS

As part of an ongoing effort to discover novel small-molecule antifolates combining the enzyme-binding species selectivity of trimethoprim (TMP) with the potency of piritrexim (PTX), 10 previously unreported 2,4-diamino-5-(2′-methoxy-5′-substituted)benzylpyrimidines (2-11) containing a carboxyl group at the distal end of the 5′-substituent were synthesized and tested as inhibitors of dihydrofolate reductase (DHFR) from Pneumocystis carinii (Pc), Toxoplasma gondii (Tg), and Mycobacterium avium (Ma), three of the opportunistic pathogens frequently responsible for life-threatening illness in people with impaired immune systems as a result of HIV infection or immunosuppressive chemotherapy. The selectivity index of DHFR inhibition was evaluated by comparing the potency of each compound against the parasite enzymes with its potency against rat liver DHFR. 2,4-Diamino-5-[5′-(5-carboxy-1-pentynyl)-2′- methoxybenzyl]pyrimidine (3) inhibited Pc DHFR with a selectivity index of 79 and was 430 times more potent than TMP. 2,4-Diamino-5-[5′-(4-carboxy-1-butynyl)-2′-methoxybenzyl] pyrimidine (2), with one less carbon than 3 in the side chain, had a selectivity index of 910 against Ma DHFR and was 43 times more potent than TMP. 2,4-Diamino-5-[5′-(5-carboxypentyl)-2′-methoxybenzyl]pyri midine (6) had a selectivity index of 490 against Tg DHFR and was 320 times more potent than TMP. 2,4-Diamino-5-[5′-(6-carboxy-1-hexynyl)-2′-methoxybenzyl] pyrimidine (4), with one more carbon than 3, was less potent against all three of the parasite enzymes than either 3 or 6 and also had a lower selectivity index than 3 against the Pc enzyme. However, 4 was the only member of the series with a selectivity index of >300 against both Tg and Ma DHFR. Given that PTX is at least 10 times more potent against rat DHFR than against P. carinii or T. gondii DHFR and that the selectivity index of several of the compounds matches or exceeds that of TMP as well as PTX, our results suggest that it may be possible to develop clinically useful nonclassical antifolates that are both potent and selective against the major opportunistic pathogens of AIDS.