Synthesis of heterobifunctional p-carborane derivatives. 3-[12- (Mercaptomethyl)-1,12-dicarba-closo-dodecaboran(12)-1-yl]propionic acid

Tetrahedron Letters

Volumn 40, Issue 28, 1999, Pages 5147-5149

  Ujváry, István ^a,b   Nachman, Ronald J ^a  

^a AGRICULTURAL RESEARCH SERVICE   (United States)

^b INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

Author keywords

Alkylation; Carboranes; Carboxylic acids and derivatives; Lithiation; Oxidation; Thiols

Indexed keywords

3 [12 (MERCAPTOMETHYL) 1,12 DICARBA CLOSO DODECABORAN(12) 1 YL]PROPIONIC ACID; CARBORANE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBOXYLATION; HYDROPHOBICITY; LIPOPHILICITY; OXIDATION; SYNTHESIS;

EID: 0033538645     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00886-2     Document Type: Article

References (17)

1. (a) Soloway, A. H.; Tjarks, W.; Barnum, B. A.; Rong, F.-G.; Barth, R. F.; Codogni, I. M.; Wilson, J. G. Chem. Rev. 1998, 98, 1515-1562.
2. (b) Hawthorne, M. F. Angew. Chem., Int. Ed. Engl. 1993, 32, 950-984.
3. Fauchère, J. L.; Do, K. Q.; Jow, P. Y. C; Mansch, C. Experientia 1980, 36, 1203-1204.
4. See for example: Escher, E.; Guillemette, G.; Leukart, O.; Regoli, D. Eur. J. Pharmacol. 1980, 66, 267-272.
5. Nachman, R. J.; Teal, P. E. A.; Radel, P. A.; Holman, G. M.; Abernathy, R. L. Peptides 1996, 17, 747-752.
6. Schöberl, U.; Magnera, T. F.; Harrison, R. M.; Fleischer, F.; Pflug, J. L.; Schwab, P. F. H.; Meng, X.; Lipiak, D.; Noll, B. C.; Allured, V. S.; Rudalevige, T.; Lee, S.; Michl, S. 7. Am. Chem. Soc. 1997, 119, 3907-3917.
7. For an early overview see: Grimes, R. N. Carboranes; Academic Press: New York, 1970; for recent works see: Viñas, C.; Cirera, M. R.; Teixidor, F.; Kivekäs, R.; Sillanpää, R.; Llibre, J. Inorg. Chem. 1998, 37, 6746-6750 and references cited therein.
8. Plešek, J.; Heømánek, S. Coll. Czech., Chem. Commun. 1979, 44, 2769-2771.
9. Oros, G.; Ujvéry, I.; Nachman, R. J. Amino Acids 1999, 17, in press.
10. Nachman, R. J.; Holman, G. M.; Haddon, W. F.; Ling, N. Science 1986, 234. 71-73.
11. +]: 264.3, observed: 264.2 (within the boron cluster envelopes).
12. Verkruijsse, H. D.; Brandsma, L. J. Organomet. Chem. 1987, 332, 95-98.
13. p-Carborane was obtained from Boron Biologicals Inc., Raleigh, NC, USA.
14. Jabre, I.; Saquet, M.; Thuillier, A. J. Chem. Res. (M) 1990, 756-784.
15. Callahan, F. M.; Anderson, G. W.; Paul, R.; Zimmerman, J. E. J. Am. Chem. Soc. 1963, 85, 201-207.
16. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 399-402.
17. Nishimura, O.; Kitada, C; Fujino, M. Chem. Pharm. Bull. 1978, 26, 1576-1585.