Aminoalkoholester von Hydroxyboranen, 10. Mitt. Tetracyclin‐Bor‐<i>Mannich</i>‐Basen als potentielle Antitumorwirkstoffe

Csük, René; Hönig, Helmut; Weidmann, Hans; Zimmerman, Howard K.

doi:10.1002/ardp.19843170410

Cited by 12 publications

(6 citation statements)

References 13 publications

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“…0.23498 (6) 0.03778 (7) 0.4847(4) 0.0453 0 (5) 0.24942 (7) 0.07727 (7) 0.5491(4) 0.0459 0 (7) 0.31678(8) 0.11059 (8) 0.6153(4) 0.0549 0 (8) 0.29208 (7) 0.13246 (7) 0.3510(4) 0.0496 0 (9) 0.28209 (6) 0.11955 (7) 0.1433(4) 0.0466 0(12) 0.32559 (6) 0.07186 (6) 0.2615 (3) 0.0366 0 (13) 0.33527 (7) 0.05078 (7) 0.3787(4) 0.0560 0 (14) 0.36694 (9) 0.04864 (8) 0.3423 (5) 0.0662 0 (15) 0.38945 (8) 0.06718 (8) 0.1891 (5) 0.0632 0 (16) 0.38116 (7) 0.08871 (7) 0.0719(4) 0.0589 0(17) 0.34962 (7) 0.09104 (6) …”

Section: Methodsunclassified

CRYSTAL AND MOLECULAR STRUCTURE OF (N->B) PHENYL [N-METHYLIMINODIACETATE-O,O',N] BORANE

Mancilla¹,

Höpfl²,

Bravo³

et al. 1997

Main Group Metal Chemistry

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The title compound, CHH12BNO4, crystallizes in a trigonal crystal system, space group R3, with two independent molecules A and Β in the asymmetric unit. These molecules show a bicyclooctane structure with different torsion angles of the junction, -22.3° (C 12 -Bi-N 6 -C 7 ) for A and 16.6° (C62-B5i-N 56 -C57) for Β and N->B coordination bond distances of 1.662 (3) and 1.673 (3) Ä, respectively. They are linked to one another by intermolecular interactions C=0 H-CH.

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Section: Methodsunclassified

CRYSTAL AND MOLECULAR STRUCTURE OF (N->B) PHENYL [N-METHYLIMINODIACETATE-O,O',N] BORANE

Mancilla¹,

Höpfl²,

Bravo³

et al. 1997

Main Group Metal Chemistry

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“…Chemical shifts (ppm) are relative to (CH 3 ) 4 Si for 1 H and 13 C and BF 3 ·OEt 2 for 11 B. Coupling constants are reported in Hz. Infrared spectra were recorded on a PerkineElmer 16F-PC FT-IR spectrometer.…”

Section: Instrumentationmentioning

confidence: 99%

Synthesis, characterization and X-ray studies of new chiral five-six-membered ring, [4.3.0] heterobicyclic system of monomeric boronates

Rivera¹,

Rincón²,

Farfán³

et al. 2011

Journal of Organometallic Chemistry

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“…Most of the compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11) were synthesized by the reactions of methyl or arylboronic acids with the cor responding dialkanolamines (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…Borocane 13 was obtained as a white powder in a yield of 0.17 g (15%). 1 (16). Ger manium ethoxide (0.25 g, 0.75 mmol) and AlCl 3 (∼0.01 g) were added to a solution of borocane 6 (0.22 g, 0.75 mmol) in toluene (15 mL).…”

Section: Methodsmentioning

confidence: 99%

“…11 B NMR, δ: 12.69. MS, m/z (I rel (%)): 357 [M] + (1), 280 [M -Ph] + (100), 265 [M -Ph -Me] + (5), 174 [M -Ph 2 CO] + (47).shows signals of two diastereomers in a ratio of 3 : 1 1. H NMR of the major isomer, δ: 2.26 (s, 3 H, NMe); 2.30-2.36 and 3.46-3.52 (both m, 1 H each, NCH 2 ); 3.88 (d, 1 H, NCH, J = 10.5 Hz); 4.14-4.18 and 4.33-4.40 (both m, 1 H each, OCH 2 ); 5.72 (d, 1 H, OCH, J = 10.5 Hz); 7.16-7.49 and 7.84-7.86 (both m, 15 H, Ph).…”

mentioning

confidence: 99%

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Synthesis and structures of new 1,3,6,2-dioxazaborocanes containing substituents in the ocane fragment

et al. 2008

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H, Ph) were synthesized by the reactions of aryl or methylboronic acids with dialkanolamines. The treatment of (Me 2 NCH 2 CH 2 O) 3 B (15) with MeN(CH 2 CH 2 OH)(CH 2 CPh 2 OH) afforded 2 [2 (dime thylamino)ethoxy] 1,3,6,2 dioxazaborocane (12). 2 Fluoro 1,3,6,2 dioxazaborocanes R 1 N(CHR 3 CHR 2 O)(CH 2 CH 2 O)BF (13: R 1 = PhCH 2 , R 2 = R 3 = H; 14: R 1 = Me, R 2 = R 3 = Ph, threo) were synthesized by the reaction of bis(trimethylsilyl) ethers of the corresponding di alkanolamines with BF 3 •Et 2 O. The new borocanes can be used for the synthesis of the corre sponding germanium derivatives PhCH 2 N(CH 2 CH 2 O) 2 GeX 2 (16, X = OEt; 17, X = Cl), as exemplified by the reaction of compound 6. The structures of erythro MeN(CH 2 CH 2 O)(CHPhCHPhO)BPh (3), threo MeN(CH 2 CH 2 O)(CHPhCHPhO)BPh (4), erythro MeN(CH 2 CH 2 O)(CHPhCHPhO)B(4 MeC 6 H 4 ) (8), and PhCH 2 N(CH 2 CH 2 O) 2 BF (13) were established by X ray diffraction. The coordination polyhedra of the boron atoms in these complexes can be described as distorted tetrahedra. The boron-nitrogen distances (1.705(7)-1.723(3) Å) provide unambiguous evidence for the presence of the B←N transannu lar interaction in these compounds. The structures of the resulting borocanes containing phenyl substituents at the carbon atoms of the ocane skeleton were studied by NMR spectroscopy and quantum chemical density functional theory calculations.

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Aminoalkoholester von Hydroxyboranen, 10. Mitt. Tetracyclin‐Bor‐Mannich‐Basen als potentielle Antitumorwirkstoffe

Cited by 12 publications

References 13 publications

CRYSTAL AND MOLECULAR STRUCTURE OF (N->B) PHENYL [N-METHYLIMINODIACETATE-O,O',N] BORANE

CRYSTAL AND MOLECULAR STRUCTURE OF (N->B) PHENYL [N-METHYLIMINODIACETATE-O,O',N] BORANE

Synthesis, characterization and X-ray studies of new chiral five-six-membered ring, [4.3.0] heterobicyclic system of monomeric boronates

Synthesis and structures of new 1,3,6,2-dioxazaborocanes containing substituents in the ocane fragment

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