Synthesis of 1-amino-3-[2-(1,7-dicarba-closo-dodecaboran(12)-1-yl)ethyl]cyclobutane-carboxylic acid: A potential BNCT agent

被引：36

作者：

Srivastava, RR

Singhaus, RR

Kabalka, GW

机构：

[1] UNIV TENNESSEE,DEPT CHEM,KNOXVILLE,TN 37996

[2] UNIV TENNESSEE,DEPT RADIOL,KNOXVILLE,TN 37996

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 13期

关键词：

D O I：

10.1021/jo970148+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of an unnatural amino add, 1-amino-3-[2-(1,17-dicarba-closo-dodecaboran(12)-1-yl)ethyl]cyclobutanecarboxylic acid, was achieved. This new potential BNCT agent was prepared via the mono alkylation of m-carborane with 4-bromobutene to produce 4-m-carboranyl-1-butene, which was then subjected to a 2 + 2 cycloaddition using dichloroketene. The resultant boronated cyclobutanone was reductively dechlorinated prior to the formation of the corresponding hydantoin, which was hydrolized to the title compound in excellent yield.

引用

页码：4476 / 4478

页数：3

共 50 条

[41] DERIVATIVES OF PYRAZOLE-1-CARBOXYLIC ACID .3. SYNTHESIS OF SOME DERIVATIVES OF N-(4-[2-(PYRAZOLE-1-CARBOXAMIDO)-ETHYL]BENZENESULPHONYL)UREA
BRZOZOWSKI, Z
MAGIELKA, S
ACTA POLONIAE PHARMACEUTICA, 1981, 38 (05): : 521 - 526
[42] Oxone((R)) -Mediated Synthesis of Benzimidazoles from 1,2Phenylenediamines and Aldehydes: Preparation of 2-(4Cyano- Phenyl)-1-[2-(3,4-Dimethoxyphenyl)-Ethyl]-1HBenzimidazole- 5-Carboxylic Acid Ethyl Ester
Gillard, James R.
Beaulieu, Pierre L.
ORGANIC SYNTHESES, 2012, 89 : 131 - 142
[43] Piperic Acid Amide of β,β-disubstituted-β-Amino Acid, 2-(4-Amino-1-Benzylpiperidin-4-yl)Acid [β3,3-Pip(Bzl)] as Cytotoxic and Apoptosis Inducing Agent
Wani, Naiem Ahmad
Rasool, Reyaz Ur
Farooq, Saleem
Shankar, Sudha
Amin, Hina
Nayak, Debasis
Koul, Surrinder
Goswami, Anindya
Rai, Rajkishor
CHEMISTRYSELECT, 2016, 1 (13): : 3657 - 3660
[44] Synthesis and X-ray structure of Zn(bpeae)ZnCl3 (bpeae=2-{Bis-[2-(3,5-dimethyl-pyrazol-1-yl)-ethyl]amino}ethoxy)
Jeong, JH
Park, YD
Roh, SG
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2003, 24 (04) : 521 - 523
[45] CYCLIZATION OF ETHYL (E)/(Z)-[2-(1-CYCLOHEXEN-1-YL)CYCLOHEXYLIDENE]CYANOACETATE TO 10-AMINO-1,2,3,4,5,6,7,8-OCTAHYDROPHENANTHRENE-9-CARBOXYLIC ACID - A ROUTE TO 1,2,3,4,5,6,7,8-OCTAHYDROPHENANTHRENE DERIVATIVES
WILAMOWSKI, J
KRASODOMSKI, W
NOWAK, B
SEPIOL, JJ
LIEBIGS ANNALEN, 1995, (08): : 1567 - 1570
[46] SYNTHESIS OF POTENTIAL METABOLITES OF ETHYL (E)-4-[2-(3,4-DIHYDRO-4,4-DIMETHYL-2H-1-BENZOPYRAN-6-YL)-1-PROPENYL]BENZOATE
SUNTHANKAR, PS
BERLIN, KD
NELSON, EC
THORNE, RL
GENO, PW
ARCHER, JC
ROLF, LL
BARTELS, KE
JOURNAL OF PHARMACEUTICAL SCIENCES, 1993, 82 (05) : 543 - 545
[47] Synthesis and crystal structure of bis [2-(3-(2-((2-hydroxybenzylidene)amino)ethyl)oxazolidin-2-yl)phenol]cerium (iv) 1,4-dioxane monosolvate
Swamy, G. Y. S. K.
Sivanarayanan, P.
MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2016, 629 (01) : 61 - 69
[48] Copolymers of 4-(1-methyl-1-mesityl-3-cyclobutyl)-2-N-1, 3-thiazole-2-yl methacrylamide with 2-[(5-methylisoxazol-3-yl) amino]-2-oxo-ethyl methacrylate: Synthesis, characterization, monomer reactivity ratios and biological activity
Erol, Ibrahim
Dedelioglu, Ayse
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2008, 46 (02) : 530 - 542
[49] Functionalization of polymethylcarboranes.: Preparation and reactivity of 2,3,4,5,6,7,8,9,10,11-decamethyl-1,12-dicarba-closo-dodecaborane(12)-1-carboxylic acid
Endo, Y
Yaguchi, K
Tsuji, M
Yamaguchi, K
Shudo, K
CHEMICAL & PHARMACEUTICAL BULLETIN, 1999, 47 (05) : 699 - 701
[50] Stereoselective synthesis and biological evaluation of syn-1-amino-3-[18F]fluorocyclobutyl-1-carboxylic acid as a potential positron emission tomography brain tumor imaging agent
Yu, Weiping
Williams, Larry
Camp, Vernon M.
Malveaux, Eugene
Olson, Jeffrey J.
Goodman, Mark M.
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (05) : 1982 - 1990

← 1 2 3 4 5 →