Steroids. Part X. A convenient synthesis of alkyl aryl ethers

Manhas, M. S.; Hoffman, W. H.; Lal, Bansi; Bose, Ajay K.

doi:10.1039/p19750000461

Cited by 73 publications

(32 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In some cases, the outcome of the reaction is extremely sensitive to the reaction conditions and to the nature of the 5-substituent of the isoquinolin-1-one; mixtures of products were never observed. Although Mitsunobu reactions with isoquinolin-1-ones as the nucleophilic component are previously unreported, Manhas et al 20 achieved reaction of quinazolin-4-ones with steroid alcohols through the exocyclic oxygen of the heterocycles. These observations are consistent with regioselectivity being controlled by the hardness/softness of the nucleophiles and electrophiles involved.…”

Section: Scheme 3 Unequivocal Synthesis Of 5-bromo-2-(4-methoxybenzylmentioning

confidence: 99%

N- and O-Alkylation of isoquinolin-1-ones in the Mitsunobu reaction: development of potential drug delivery systems

Ferrer

Naughton

Parveen

et al. 2002

J. Chem. Soc., Perkin Trans. 1

View full text Add to dashboard Cite

Regioselective methods were investigated to prepare N-and O-alkylated isoquinolin-1-ones efficiently. The predicted regioselective alkylation of the nitrogen with (hetero)benzyl halides was complemented using (hetero)benzylic Mitsunobu electrophiles to alkylate predominantly at the oxygen. A series of drug-delivery conjugates was prepared demonstrating control over the site of alkylation. The Mitsunobu reaction provides a new approach to 1-alkoxyisoquinolines that were unavailable via previous harsher synthetic methods.

show abstract

Section: Scheme 3 Unequivocal Synthesis Of 5-bromo-2-(4-methoxybenzylmentioning

confidence: 99%

N- and O-Alkylation of isoquinolin-1-ones in the Mitsunobu reaction: development of potential drug delivery systems

Ferrer

Naughton

Parveen

et al. 2002

J. Chem. Soc., Perkin Trans. 1

View full text Add to dashboard Cite

show abstract

“…The dianix yellow 5R (2) is converted to ether (3) through Mitsunobu reaction [13] with 1,2-Oisopropylideneglycerol (solketal, 1) (Scheme 1). Removing of the acetonide protecting group with an acid yields the title compound (4).…”

Section: Resultsmentioning

confidence: 99%

3-{4-[(E)-{4-[(E)-Phenyldiazenyl]phenyl}diazenyl]phenoxy}propane-1,2-diol

Chupin

Болдырев

2017

Molbank

View full text Add to dashboard Cite

Abstract:Title compound was designed to be a black quencher of pyrene fluorescence. It was made amphiphilic to serve as a membrane-bound probe. The synthesis is a two-step procedure. The first step is a Mitsunobu reaction of [{(phenyldiazenyl)phenyl}diazenyl]phenol with 1,2-O-isopropylideneglycerol. The second step is the cleavage of the isopropylidene protecting group. The title compound has the extinction coefficient 59,000 at λmax = 380 nm. The Forster distance between the title compound and the pyrene was found to be 37.8 Å.

show abstract

“…NFPS ethyl ester was synthesized by the following sequence of reactions: N-alkylation of sarcosine ethyl ester with 3-chloro-4Ј-fluoropropiophenon, reduction of the carbonyl group with sodium borohydride, and dehydration with 2-phenylphenol using triphenylphosphine and diethyl azodicarboxylate (Manhas et al, 1975). The chemical structure of the product was identified by 1 H-NMR, mass spectrum, and elemental analysis to be NFPS ethyl ester.…”

Section: Methodsmentioning

confidence: 99%

Effects of endogenous agonists, glycine and D‐serine, on in vivo specific binding of [¹¹C]L‐703,717, a PET radioligand for the glycine‐binding site of NMDA receptors

Haradahira¹,

Okauchi²,

Maeda³

et al. 2003

Synapse

View full text Add to dashboard Cite

A positron-emitter (carbon-11) labeled antagonist for the glycine-binding site of NMDA receptors, [(11)C]L-703,717, has a unique in vivo binding characteristic, in which it preferentially binds to cerebellar-specific NMDA receptors consisting of a GluRepsilon3 subunit and eventually accumulates in rodent cerebellum under in vivo conditions, but not under in vitro conditions. In order to understand the in vivo-specific site and subunit localization of this radioligand, we examined the effect of the endogenous glycine site agonists, glycine and D-serine, on in vivo [(11)C]L-703,717 binding. An increase in extracellular glycine concentration by treatment with a glycine transporter 1 (GlyT1)-selective inhibitor, NFPS ethyl ester, significantly decreased the cerebellar localization of [(11)C]L-703,717 in rats. D-serine is known to be concentrated in mammalian forebrain regions. The lack of D-serine detection in the cerebellum may be due to the fact that it has the highest enzymatic activity of D-amino acid oxidase (DAO). It was found that the cerebellar localization of [(11)C]L-703,717 is greatly diminished in mutant mice lacking DAO, in which D-serine content in the cerebellum is drastically increased from a nondetectable level in normal mice. These studies indicate that [(11)C]L-703,717 is susceptible to inhibition by glycine site agonists in its in vivo binding, and suggest that regional differences in inhibitions by endogenous agonists may be a crucial factor in the site- and subunit-specific binding of this glycine-site antagonist.

show abstract

Steroids. Part X. A convenient synthesis of alkyl aryl ethers

Cited by 73 publications

References 0 publications

N- and O-Alkylation of isoquinolin-1-ones in the Mitsunobu reaction: development of potential drug delivery systems

N- and O-Alkylation of isoquinolin-1-ones in the Mitsunobu reaction: development of potential drug delivery systems

3-{4-[(E)-{4-[(E)-Phenyldiazenyl]phenyl}diazenyl]phenoxy}propane-1,2-diol

Effects of endogenous agonists, glycine and D‐serine, on in vivo specific binding of [¹¹C]L‐703,717, a PET radioligand for the glycine‐binding site of NMDA receptors

Contact Info

Product

Resources

About

Steroids. Part X. A convenient synthesis of alkyl aryl ethers

Cited by 73 publications

References 0 publications

N- and O-Alkylation of isoquinolin-1-ones in the Mitsunobu reaction: development of potential drug delivery systems

N- and O-Alkylation of isoquinolin-1-ones in the Mitsunobu reaction: development of potential drug delivery systems

3-{4-[(E)-{4-[(E)-Phenyldiazenyl]phenyl}diazenyl]phenoxy}propane-1,2-diol

Effects of endogenous agonists, glycine and D‐serine, on in vivo specific binding of [11C]L‐703,717, a PET radioligand for the glycine‐binding site of NMDA receptors

Contact Info

Product

Resources

About

Effects of endogenous agonists, glycine and D‐serine, on in vivo specific binding of [¹¹C]L‐703,717, a PET radioligand for the glycine‐binding site of NMDA receptors