2'-Deoxycytidine-N3-cyanoborane

Gao, Qi; Sood, Anoop K.; Shaw, Barbara Ramsay; Williams, Loren Dean

doi:10.1107/s0108270195013783

Cited by 4 publications

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“…The crystal structure shows that the B-atom is tetrahedral with bond angles ranging from 107.9(3) to 111.7(3)°. The B-C=N moiety has a bent geometry as indicated by the angle 174.0(3) which is consistent with 176.0(3)° in the case of 2'-deoxycytidine-N(3)cyanoborane [7], The bond lengths and the bond angles in the o-toluidine ring are well within the distances expected for the toluidine moiety and deserve no special comment. Compound 1, in addition to its potential as an anti-neoplastic agent, may also be useful in Boron Neutron Capture Therapy (BNCT).…”

Section: Commentsupporting

confidence: 70%

Crystal Structure of an Anti-Neoplastic Agent, O-Toluidinecyanoborane, C8h11bn2

Vyakaranam¹,

Rana²,

Zheng³

et al. 2002

Main Group Metal Chemistry

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Figure 1. Molecular structure (50% displacement ellipsoids) of CSHMBNI. The selected bond distances and angles are: B- CommentWe have previously reported the synthesis and cytotoxic activity of amine-borane adducts of aliphatic heterocyclic amines in murine and human tumor cells [1][2][3][4]. The cyano-, carboxy-, carbomethoxy-, and the carbamoylborane adducts of piperidines, piperazines, morpholines and imidazoles were shown to be potent cytotoxic agents in L-1210, Tmolt 3 , and HeLa-S' suspended cells [5]. The cyano-and carboxyborane adducts of cyclohexylamines and toluidines were also shown to be cytotoxic towards suspended single cell tumors [6]. Several of these compounds were active at 8mg/Kg/day I. P. in the Ehrlich ascites carcinoma screen in-vivo.The

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Section: Commentsupporting

confidence: 70%

Crystal Structure of an Anti-Neoplastic Agent, O-Toluidinecyanoborane, C8h11bn2

Vyakaranam¹,

Rana²,

Zheng³

et al. 2002

Main Group Metal Chemistry

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“…The title nucleoside has been crystallized in a different crystal system by Gao, Sood, Shaw & Williams (1996). Some of the X-ray results described here have been used recently in theoretical computations on intramolecular non-bonded H...H interactions between the mNH2 and mBH2CN group H atoms (Zottola, Pedersen, Singh & Shaw, 1994).…”

Section: Introductionmentioning

confidence: 99%

2'-Deoxycytidine-N(3)-cyanoborane Monohydrate

Singh¹,

Zottola²,

Huang³

et al. 1996

Acta Crystallogr C

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The structure of the title compound, [4-amino-l-(2-deoxy-fl-D-ribofuranosyl)-2-oxo-1H-3-pyrimidinio]-(cyano)borate, C10H15BNnOa.H20, features an interaction of 2.05 (4)/k between an H atom of the --BH2CN group and an H atom of the --NH2 group. The ~N group does not lie in the cytosine plane, the N atom being 2.24 ,~ away from the plane. The cytosine tings are stacked with almost complete overlap along the twofold screw axis with an interplanar separation of 4.03/~. The sugar is in the ~T puckering mode, the C(5')--O(5') bond has the gg conformation and the relative orientation of the sugar and the base is anti.In order to provide more insight into the structureactivity relationships of cyanoborane nucleosides we have started a program of research on the structure of these nucleosides using X-ray diffraction and ab initio molecular-orbital (MO) calculations. The title nucleoside has been crystallized in a different crystal system by Gao, Sood, Shaw & Williams (1996). Some of the X-ray results described here have been used recently in theoretical computations on intramolecular non-bonded H...H interactions between the mNH2 and mBH2CN group H atoms (Zottola, Pedersen, Singh & Shaw, 1994).The The pyrimidine ring is planar, although the deviations of the atoms from the mean plane are somewhat CommentCyanoborane analogs of 2'-deoxynucleosides such as the title compound, (I), show in vivo antineoplastic activity against various tumors (Sood, Spielvogel & Shaw, 1989;Sood, Spielvogel, Shaw, Carlton, Burnham, Hall & Hall, 1992). In addition, the title compound has potential use in boron neutron-capture therapy (BNCT) since it tends to concentrate quite effectively in rapidly divid'.mg cancer cells (Sood et al., 1992). The BNCT technique has been used recently in the treatment of brain cancer (see, for example, Science, 17 February 1995, Vol. 267, p. 956 and 23 September 1994, Vol. 265, p. 1799). (Johnson, 1965) drawing of the nucleoside showing 50% probability displacement ellipsoids and the atom-numbering scheme. H atoms are shown as small circles of arbitrary size.

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“…Gaussian Inc., Pittsburgh, PA, USA. Gao, Q., Sood, A., Shaw, B. R. & Williams, L. D. (1996). Acta Cryst.…”

Section: Introductionmentioning

confidence: 99%

L-Histidine Methyl Ester Dihydrochloride

Vilchiz

Norman²,

Chang³

1996

Acta Crystallogr C

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The title compound, C7H13N3022+.2C1 -, has distances and angles quite similar to those of histidine hydrochloride monohydrate [Donohue & Caron (1964). Acta Cryst. 17, 1178Cryst. 17, -1180, except for the distances within the ester functionality. Am. Chem. Soc. 94,8212. Frisch, M. J., Head-Gordon, M., Trucks, G. W., Foresman, J., Schlegel, H., Raghavachari, K., Robb, M. S., Binkley, J. S., Gonzalez, C., Defrees, D. J., Fox, D. J., Whiteside, R. A., Seeger, R., Melius, C. F., Baker, J., Martin, R. L., Kahn, L. R., Stewart, J. J. P., Topiol, S. & Pople, J. A. (1992). GAUSSIAN92. Gaussian Inc., Pittsburgh, PA, USA. Gao, Q., Sood, A., Shaw, B. R. & Williams, L. D. (1996). Acta Cryst.C52. In the press. Johnson, C. K. (1965 11 mmol) were refluxed for 8 h in 300 ml of tetrahydrofuran. The mixture was allowed to cool. The resulting solids were collected by vacuum filtration and recrystallized from water. Symmetry codes: (i) 1 + x, y, z; (ii) 1 -x, y -½, -1 -z. Crystal dataThe absolute configuration was fixed by the use of L-histidine in the 'synthesis'. Inversion of the structure and refinement of the D configuration gave a slightly poorer agreement (R = 0.0329, wR = 0.0346 and S = 1.88). Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988 We are grateful to the Kresge Foundation for providing the funds for the purchase of the diffractometer used in this work.

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2'-Deoxycytidine-N3-cyanoborane

Abstract: The structure of the P2~212~ form of 2'-deoxycytidine-N3-cyanoborane, C~0H15BN404, has been determined. The sugar is in the 2E puckering mode and the C5'---O5' bond has a tg conformation while the relative orientation of the sugar and the base remains anti.

Cited by 4 publications

References 1 publication

Crystal Structure of an Anti-Neoplastic Agent, O-Toluidinecyanoborane, C8h11bn2

Crystal Structure of an Anti-Neoplastic Agent, O-Toluidinecyanoborane, C8h11bn2

2'-Deoxycytidine-N(3)-cyanoborane Monohydrate

L-Histidine Methyl Ester Dihydrochloride

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