68239-22-5

Usage

Synonym

(S)-HPHPD

Classification

Pyrrolidine-2,5-dione derivative

Parent compound

Amino acid proline

Potential pharmaceutical application

Inhibitor of prolyl hydroxylase enzyme

Enzyme target

Prolyl hydroxylase

Enzyme function

Regulation of hypoxia-inducible factor (HIF)

HIF role

Oxygen homeostasis regulation

Associated diseases

Cancer, ischemic heart disease

Therapeutic potential

Treatment of conditions related to HIF pathway modulation

Current status

Further research needed to understand potential uses and mechanisms of action

InChI:InChI=1/C12H13NO3/c14-10(9-4-2-1-3-5-9)8-13-11(15)6-7-12(13)16/h1-5,10,14H,6-8H2

Upstream product

• 123-56-8 Succinimide 
• 96-09-3 styrene oxide 
• 54553-14-9 succinic acid N-(chloromethyl)imide 
• 100-52-7 benzaldehyde 

Downstream Products

• 120542-02-1 N-[(E)-2-phenylvinyl]succinimide 
• 79365-85-8 bis-(β-hydroxy-phenethyl)-amine 
• 110057-85-7 tris-(β-hydroxy-phenethyl)-amine 
• 91974-40-2 1-(2-(4-nitrophenyl)-2-oxoethyl)pyrrolidine-2,5-dione 
• 7568-93-6 2-Amino-1-phenylethanol 
• 99989-77-2 N-(4-nitro-β-nitryloxy-phenethyl)-succinimide 
• 106272-54-2 N-(β-acetoxy-phenethyl)-succinimide 

Relevant academic research and scientific papers

Preparation and Reactivity of Highly Functionalized Organometallics at the α Position of Oxygen or Nitrogen

α-Halogenoalkyl carboxylates (FG-R1CH(X)(OCOR2); FG = COOR, CN, SR; X = I, Br) were readily prepared by the addition of an acid chloride or bromide (R2COX; X = Br or Cl) to an aldehyde (FG-RCHO) in the presence of a catalytic amount of ZnCl2.They insert efficiently zinc dust in THF-DMSO (X = Br, 8 - 10 deg C, 6 - 10 h) affording the corresponding zinc organometallics at the α position to oxygen FG-RCH(ZnBr)(OAc).After the addition of the THF-soluble copper salt CuCN*2LiCl, the corresponding copper reagents FG-RCH(Cu(CN)ZnBr)(OAc) are formed and reacted with variousclasses of electrophiles such as acid chlorides, aldehydes, enones, allylic and alkynyl halides, activated alkynes, nitro olefins and alkylidenemalonates providing polyfunctional molecules in excellent yields.Similarly, zinc organometallics at the α position to the nitrogen of cyclic imides were prepared by the zinc insertion to cyclic α-chloromethyl (or α-chloroethyl) imides.After their transmetalation to the corresponding copper organometallic ((R1CO)2NCH(R)(Cu(CN)ZnCl); R = Me or H), they were reacted with allylic and alkynyl halides and ethyl propiolate affording polyfunctional imides.The reaction of cyclic N-(chloromethyl)imides with aldehydes in the presence of chromium(II) chloride in THF furnishes protected amino alcohols in 36 - 95percent yield.

Base-catalyzed carbon-carbon bond formation reactions of ω-hydroxylactams

Active methylene compounds such as methyl ketones, 1,3-dicarbonyl systems and nitromethane condense under the influence of base with ω-hydroxylactams, thereby forming α-alkylated nitrogen heterocycles.The ease of alkylation is detemined by the position of a tautomeric equilibrium between ω-hydroxylactam and the open-chain amide-aldehyde, which is dependent upon the type of N-substituent and upon the lactam ring size.Some applications for the products obtained are indicated.