SCOPUS 정보 검색 플랫폼

Volumn 31, Issue 39, 1990, Pages 5591-5594

Peptidic α-hydroxy phosphinyls C-terminal modification methodology

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0025041777 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)97904-8 Document Type: Article

Times cited : (119)

References (15)

1
- 0024987959
- the preceeding conmmunication
- (1990) Tetrahedron Lett. , vol.31 , pp. 5587
- Patel¹ Rielly-Gauvin² Ryono³

2
- 0021681698
- As a classic example, the 1,2-amino alcohol functionality was originally developed as a transition state mimic for developing novel and potent inhibitors of the zinc metalloprotease ACE
- (1984) Biochem. Biophys. Res. Commun. , vol.124 , pp. 141
- Natarajan¹ Gordon² Sabo³ Godfrey⁴ Weller⁵ Puscec⁶ Rom⁷ Cushman⁸

3
- 84918164793
- which was later on applied for designing renin inhibitors, C.M. Deber, V.J. Hruby, K.D. Kopple, Pierce Chemical Co, Rockford
- (1985) Peptides: Structure and Function. Proceedings of the Ninth American Peptide Symposium , vol.11 , pp. 739
- Ryono¹ Free² Neubeck³ Samaniego⁴ Godfrey⁵ Petrillo⁶

4
- 0025361445
- and more recently, for preparing potent inhibitors of the HIV protease
- (1990) J. Med. Chem. , vol.33 , pp. 1285
- Rich¹ Green² Toth³ Marshall⁴ Kent⁵

6
- 84918597177
- It is noteworthy to realize that treatment of 3 with 2-methoxypropene afforded only the uncyclized mixed ketal 15 and attempts at converting 15 to 4 were unsuccessful.

7
- 0001393796
- (1981) Tetrahedron , vol.37 , pp. 1727
- Jacques¹ Leclercq² Brienne³

8
- 84918614199
- Numerous attempts at reacting 4 with either p-nitrophenol or thiophenol using diisopropylethylamine as a base, DCC or DCC/HOBt or DCC/DMAP (cat. or equiv.) or DCC/PPY (cat. or equiv.) as the coupling agent and THF or DMF or pyridine as a solvent at room temperature or refluxing conditions failed to give the desired activated esters in significant amounts.

9
- 84918610982
- The standard conditions for forming acid chlorides (direct treatment of 4 with thionyl chloride or oxalyl chloride) generate HCl and are unsuitable for the acid sensitive phosphonic acid 4.

10
- 84918633911
- 3 for converting phosphonic acids to their phosphonochloridates under neutral conditions was brought to our attention by Dr. D. S. Karanewsky and Dr. S. Billet at Squibb.

12
- 84918612206
- For a general review on transition state analog inhibitors of proteolytic enzymes, see Rich, D.H. Peptidase Inhibitors. Comprehensive Medicinal Chemistry; Sammes, P.G.,Ed.;, Pergamon Press: Oxford, vol. 2, in press and references therein.

13
- 84918603535
- 4 oxidations under aqueous or phase transfer conditions were also less satisfactory (20–25%).

14
- 84918639682
- A more direct route sketched below for preparing 14 was also attempted but the yields were only modest.

15
- 84918599805
- The renin inhibitory activity of analogs derived from 4, 13 and 14 will be reported elsewhere.

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