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Journal articles on the topic 'Carba analogue'

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Published: 9 March 2023

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1

Thuring, Jan Willem J. F., Gerard H. L. Nefkens, and Binne Zwanenburg. "Synthesis and Biological Evaluation of the Strigol Analogue Carba-GR24." Journal of Agricultural and Food Chemistry 45, no. 4 (April 1997): 1409–14. http://dx.doi.org/10.1021/jf960443f.

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2

Boyer, Paul L., B. Christie Vu, Zandrea Ambrose, John G. Julias, Svenja Warnecke, Chenzhong Liao, Chris Meier, Victor E. Marquez, and Stephen H. Hughes. "The Nucleoside Analogue D-carba T Blocks HIV-1 Reverse Transcription." Journal of Medicinal Chemistry 52, no. 17 (September 10, 2009): 5356–64. http://dx.doi.org/10.1021/jm801176e.

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3

Lefoix, Myriam, Arnaud Tatibouët, Sylvain Cottaz, Hugues Driguez, and Patrick Rollin. "Carba-glucotropaeolin: the first non-hydrolyzable glucosinolate analogue, to inhibit myrosinase." Tetrahedron Letters 43, no. 16 (April 2002): 2889–90. http://dx.doi.org/10.1016/s0040-4039(02)00463-x.

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4

Zhang, Xini, Bradley J. Berger, and Peter Ulrich. "Synthesis and trypanocidal activity of the bis-carba analogue of pentamidine." Bioorganic & Medicinal Chemistry Letters 6, no. 9 (May 1996): 1035–36. http://dx.doi.org/10.1016/0960-894x(96)00168-0.

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5

Tilbrook, Matthew G., Robert V. Stick, and Spencer J. Williams. "β-Acarbose. VII. Approaches Towards the Synthesis of Some N-Linked Carba-Oligosaccharides." Australian Journal of Chemistry 52, no. 9 (1999): 885. http://dx.doi.org/10.1071/ch99030.

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3,4-Anhydro-1,6-dideoxy-1,6-episeleno-β-D-glucose was treated with cyclohexylamine to afford an amino diol which was subsequently converted into a cyclic carbamate, a compound shown to be a moderately successful glycosyl donor. Treatment of the same 3,4-anhydro sugar and the 1,6-epithio analogue with a 1-epivalienamine derivative afforded the corresponding secondary amines which were converted into the analogous cyclic carbamates. The epithio analogue was unsuccessful as a glycosyl donor, failing to glycosylate a carbohydrate alcohol. On the other hand, the episeleno compound appeared to function as a glycosyl donor but decomposition of the product occurred under the conditions necessary for its isolation.

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6

Atke, Anders, and Hans Vilhardt. "Uterotonic activity and myometrial receptor affinity of 1-deamino-1-carba-2-tyrosine(O-methyl)-oxytocin." Acta Endocrinologica 115, no. 1 (May 1987): 155–60. http://dx.doi.org/10.1530/acta.0.1150155.

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Abstract. The contractile effect of the analogue 1-deamino-1-carba-2-tyrosine(O-methyl)-oxytocin (carbetocin) on isolated myometrial strips from rats was compared with that of oxytocin. The uterotonic activity of the analogue was 15 ± 3 IU/mg as compared with 438 ± 41 for oxytocin, however, the response was more prolonged and could not be abolished by washing of the preparation. Despite the low biological activity of carbetocin, its binding affinity to receptors of isolated myometrial plasma membranes was of the same order of magnitude as that of oxytocin. On the basis of the present results it is concluded that a longer half-life of the analogue at the receptor compartment may be a contributing factor to the prolonged uterotonic effect observed in vivo.

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7

Campbell, Malcolm M., Malcolm Sainsbury, Philip A. Searle, and Gareth M. Davies. "Synthesis of methyl (−)-homogabaculinate and a carba analogue of 5-enolpyruvylshikimic acid." Tetrahedron Letters 33, no. 22 (May 1992): 3181–84. http://dx.doi.org/10.1016/s0040-4039(00)79846-7.

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8

Lefoix, Myriam, Arnaud Tatibouet, Sylvain Cottaz, Hugues Driguez, and Patrick Rollin. "ChemInform Abstract: Carba-glucotropaeolin: The First Non-Hydrolyzable Glucosinolate Analogue, to Inhibit Myrosinase." ChemInform 33, no. 32 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200232204.

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9

Hřebabecký, Hubert, and Antonín Holý. "Synthesis of Carbocyclic 4'-C-Hydroxymethyl Analogues of Azidodeoxythymidine, Deoxythymidine, Deoxydidehydrothymidine and Thymidine Carba Analogue with Fused Oxetane Ring." Collection of Czechoslovak Chemical Communications 65, no. 3 (2000): 395–406. http://dx.doi.org/10.1135/cccc20000395.

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Tosylation of (±)-1-[trans-4-hydroxy-3,3-bis(hydroxymethyl)cyclopentyl]-5-methylpyrimidine-2(1H),4(3H)-dione (1) and (±)-1-[cis-4-hydroxy-3,3-bis(hydroxymethyl)cyclopentyl]-5-methylpyrimidine-2(1H),4(3H)-dione (2) and treatment of the obtained 1-{(1R*,3R*,4S*)- 4-hydroxy-3-(hydroxymethyl)-3-[(tosyloxy)methyl]cyclopentyl}-5-methylpyrimidine- 2(1H),4(3H)-dione (6) and 1-{(1R*,3S*,4R*)-4-hydroxy-3-(hydroxymethyl)-3-[(tosyloxy)- methyl]cyclopentyl}-5-methylpyrimidine-2(1H),4(3H)-dione (9) with methanolic sodium methoxide gave 1-[(1R*,4S*,6S*)-4-hydroxymethyl-2-oxabicyclo[3.2.0]hept-6-yl]-5-methylpyrimidine-2(1H),4(3H)-dione (7) and 1-[(1R*,4S*,6R*)-4-hydroxymethyl-2-oxabicyclo[3.2.0]hept-6-yl]-5-methylpyrimidine-2(1H),4(3H)-dione (10), respectively. Treatment of (±)-1-{cis-4-mesyloxy-3,3-bis[(trityloxy)methyl]cyclopentyl}-5-methylpyrimidine-2(1H),4(3H)-dione (11), which was prepared from 2 by tritylation and mesylation, with 1,8-diazabicyclo[5.4.0]undec-7-ene in dimethylformamide afforded after deprotection (±)-1-[4,4-bis(hydroxymethyl)cyclopent-2-en-1-yl]-5-methylpyrimidine-2(1H),4(3H)-dione (14). Hydrogen- ation of 14 led to (±)-1-[3,3-bis(hydroxymethyl)cyclopentyl]-5-methylpyrimidine-2(1H),4(3H)- dione (15). (±)-1-{trans-4-Mesyloxy-3,3-bis[(trityloxy)methyl]cyclopentyl}-5-methylpyrimidine- 2(1H),4(3H)-dione (17), which was prepared from 1, was converted to (1R*,9R*)-6-methyl-5-oxo-11,11-bis(trityloxymethyl)-2-oxa-4,8-diazatricyclo[7.2.1.03,8]dodec-3,6-diene (18). The compound 18 was deprotected and heated with lithium azide in dimethylformamide to give (±)-1-[trans-4-azido-3,3-bis(hydroxymethyl)cyclopentyl]-5-methylpyrimidine-2(1H),4(3H)-dione (21).

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10

Norström, Anders, Ann Andersson, and Hans Vilhardt. "Contractile effect of oxytocin and 1-deamino-1-carba-2-tyrosine (O-methyl)-oxytocin in myometrial tissue from non-pregnant and term pregnant women." Acta Endocrinologica 122, no. 5 (May 1990): 566–68. http://dx.doi.org/10.1530/acta.0.1220566.

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Abstract. The contractile effect of the analogue 1-deamino-1-carba-2-tyrosine (O-methyl)-oxytocin (carbetocin) on isolated strips from the human myometrium was compared with that of oxytocin. Neither oxytocin nor carbetocin affected contractile activity in strips from nonpregnant women, but both peptides stimulated contractile activity in strips from women at term pregnancy (2× 10−11 mol/l, and 10−10 mol/l, respectively). Thus, carbetocin is almost as potent as oxytocin with regard to stimulating myometrial contractions at term.

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11

Wyatt, P. G., A. S. Anslow, B. A. Coomber, R. P. C. Cousins, D. N. Evans, V. S. Gilbert, D. C. Humber, et al. "A Short High Yielding Synthesis of the Potent Anti-VZV Carbocyclic Nucleoside Analogue Carba-BVDU." Nucleosides and Nucleotides 14, no. 9-10 (November 1995): 2039–49. http://dx.doi.org/10.1080/15257779508010722.

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12

Neunert, Grażyna, Jolanta Tomaszewska-Gras, Aneta Baj, Marlena Gauza-Włodarczyk, Stanislaw Witkowski, and Krzysztof Polewski. "Phase Transitions and Structural Changes in DPPC Liposomes Induced by a 1-Carba-Alpha-Tocopherol Analogue." Molecules 26, no. 10 (May 11, 2021): 2851. http://dx.doi.org/10.3390/molecules26102851.

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Steady-state emission spectroscopy of 1-anilino-8- naphthalene sulfonate (ANS) and 1,6-diphenyl-1,3,5-hexatriene (DPH), fluorescence anisotropy, and DSC methods were used to characterize the interactions of the newly synthesized 1-carba-alpha-tocopherol (CT) with a 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) membrane. The DSC results showed significant perturbations in the DPPC structure for CT concentrations as low as 2 mol%. The main phase transition peak was broadened and shifted to lower temperatures in a concentration-dependent manner, and pretransition was abolished. Increasing CT concentrations induced the formation of new phases in the DPPC structure, leading to melting at lower temperatures and, finally, disruption of the ordered DPPC structure. Hydration and structural changes of the DPPC liposomes using ANS and DPH fluorescent probes, which are selectively located at different places in the bilayer, were studied. With the increased concentration of CT molecules in the DPPC liposomes, structural changes with the simultaneous formation of different phases of such mixture were observed. Temperature studies of such mixtures revealed a decrease in the temperature of the main phase transition and fluidization at decreasing temperatures related to increasing hydration in the bilayer. Contour plots obtained from concentration–temperature data with fluorescent probes allowed for identification of different phases, such as gel, ordered liquid, disordered liquid, and liquid crystalline phases. The CT molecule with a modified chromanol ring embedded in the bilayer led to H-bonding interactions, expelling water molecules from the interphase, thus introducing disorder and structural changes to the highly ordered gel phase.

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13

Desai, Dhimant H., Azzouz Ben Cheikh, and Jiri Zemlicka. "One-pot synthesis of (±)-1′a-carba-1′aβ-hydroxycytidine - a new carbocyclic analogue of cytidine." Tetrahedron Letters 32, no. 44 (October 1991): 6281–84. http://dx.doi.org/10.1016/0040-4039(91)80147-x.

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14

Hlozek, Jason, Neil Ravenscroft, and Michelle M. Kuttel. "Modeling the conformations of Neisseria meningitidis serogroup a CPS and a carba-analogue: Implications for vaccine development." Carbohydrate Research 486 (December 2019): 107838. http://dx.doi.org/10.1016/j.carres.2019.107838.

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15

Altman, Molly K., Vashisht Gopal, Wei Jia, Shuangxing Yu, Hassan Hall, Gordon B. Mills, A. Cary McGinnis, et al. "Targeting melanoma growth and viability reveals dualistic functionality of the phosphonothionate analogue of carba cyclic phosphatidic acid." Molecular Cancer 9, no. 1 (2010): 140. http://dx.doi.org/10.1186/1476-4598-9-140.

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16

WYATT, P. G., A. S. ANSLOW, B. A. COOMBER, R. P. C. COUSINS, D. N. EVANS, V. S. GILBERT, D. C. HUMBER, et al. "ChemInform Abstract: A Short High Yielding Synthesis of the Potent anti-VZV Carbocyclic Nucleoside Analogue Carba-BVDU." ChemInform 27, no. 16 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199616264.

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17

K. Gurjar, Mukund, Mukund S. Chorghade, Challa Nageswar Reddy, and Uttam R. Kalkote. "Studies toward the Total Synthesis of Carba Analogue of Motif C of M. TB Cell Wall AG Complex." HETEROCYCLES 77, no. 2 (2009): 909. http://dx.doi.org/10.3987/com-08-s(f)59.

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18

DESAI, D. H., A. B. CHEIKH, and J. ZEMLICKA. "ChemInform Abstract: One-Pot Synthesis of (.+-.)-1′a-Carba-1′aβ-hydroxycytidine. A New Carbocyclic Analogue of Cytidine." ChemInform 23, no. 26 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199226283.

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19

Hrebabecky, Hubert, and Antonin Holy. "ChemInform Abstract: Synthesis of Carbocyclic 4′-C-Hydroxymethyl Analogues of Azidodeoxythymidine (XIV), Deoxythymidine (IX), Deoxydidehydrothymidine (VII) and Thymidine Carba Analogue with Fused Oxetane Ring (V)." ChemInform 31, no. 29 (June 7, 2010): no. http://dx.doi.org/10.1002/chin.200029203.

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20

Legnani, Laura, Silvia Ronchi, Silvia Fallarini, Grazia Lombardi, Federica Campo, Luigi Panza, Luigi Lay, et al. "Synthesis, molecular dynamics simulations, and biology of a carba-analogue of the trisaccharide repeating unit of Streptococcus pneumoniae 19F capsular polysaccharide." Organic & Biomolecular Chemistry 7, no. 21 (2009): 4428. http://dx.doi.org/10.1039/b911323a.

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21

Cort, N., A. Kunavongkrit, H. Kindahl, and S. Einarsson. "The Effect of a Long-Acting Carba Analogue of Oxytocin on Prostaglandin F2α Metabolite Levels During the Oestrous Cycle in Swine." Zentralblatt für Veterinärmedizin Reihe A 31, no. 1-10 (May 13, 2010): 489–98. http://dx.doi.org/10.1111/j.1439-0442.1984.tb01308.x.

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22

Sjöquist, P. O. B., L. Mårtensson, L. Bjellin, and A. M. Carter. "Actions of a New Vasopressin Analogue (1-deamino-6-carba-[8-arginine]-vasopressin) on Regional Blood Flow in Pregnant Guinea Pigs." Acta Pharmacologica et Toxicologica 43, no. 3 (March 13, 2009): 190–95. http://dx.doi.org/10.1111/j.1600-0773.1978.tb02254.x.

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23

Ledvina, Miroslav, Radka Pavelova, Anna Rohlenova, Jan Jezek, and David Saman. "ChemInform Abstract: Synthesis of Normuramic Acid Carba Analogue and Its Glycopeptide Derivative Resistant to β-Elimination Splitting of the Side Chain." ChemInform 32, no. 20 (May 15, 2001): no. http://dx.doi.org/10.1002/chin.200120172.

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24

Veis, J. H., M. A. Dillingham, and T. Berl. "Effects of prostacyclin on the cAMP system in cultured rat inner medullary collecting duct cells." American Journal of Physiology-Renal Physiology 258, no. 5 (May 1, 1990): F1218—F1223. http://dx.doi.org/10.1152/ajprenal.1990.258.5.f1218.

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Rat inner medullary collecting tubule (RIMCT) cells produce arachidonate derivatives including prostacyclin (PGI2). In RIMCT cells, PGI2 causes a dose-dependent increase in adenosine 3',5'-cyclic monophosphate (cAMP; fmol/micrograms protein) from a basal level of 15.6 +/- 1.7 to 32.4 +/- 5.7 at 0.3 microM, 63.3 +/- 8.3 at 3 microM, and 103.5 +/- 9.4 at 30 microM PGI2. At concentrations of arginine vasopressin (AVP) from 10(-7) to 10(-9) M, cAMP was greater in the presence than absence of 3 microM PGI2, suggesting independent sites of action. To assess whether the PGI2 effect is mediated by the prostaglandin E2 (PGE2) receptor, desensitization studies were performed. A 6-h preincubation with 10 microM PGE2 blunted the response to 3 microM PGE2 by 90 +/- 2% but the PGI2 response was decreased by only 31 +/- 5%, P less than 0.001. Carbaprostacyclin (carba-PGI2), a stable analogue of PGI2, blunted the cAMP response to PGI2 by 94 +/- 3% but to PGE2 by only 46 +/- 7%, P less than 0.005. The postreceptor effect of PGI2 on components of the adenylate cyclase was examined. The response to forskolin was markedly potentiated by PGI2. PGI2 (3 microM) caused an increase in cAMP of 67 fmol/micrograms over basal in the absence of forskolin, of 164 fmol/micrograms at 10(-7) M forskolin, of 386 fmol/micrograms at 10(-6) M forskolin, and of 563 fmol/micrograms at 10(-5) M forskolin. The response of PGI2 was likewise potentiated by forskolin. Water permeability alone or in response to AVP in isolated perfused inner medullary collecting tubules was not affected by carba-PGI2.(ABSTRACT TRUNCATED AT 250 WORDS)

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25

Chansel, D., J. C. Dussaule, N. Ardaillou, and R. Ardaillou. "Identification and regulation of renin in human cultured mesangial cells." American Journal of Physiology-Renal Physiology 252, no. 1 (January 1, 1987): F32—F38. http://dx.doi.org/10.1152/ajprenal.1987.252.1.f32.

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Renin activity was measured in the incubation medium, and the cellular extract of human mesangial cells, which had been cultured in the presence of renin-free human plasma (three kidneys; 4-7 passages). Active renin and total renin obtained after trypsin treatment was estimated by radioimmunoassay of angiotensin I using renin-free human plasma as a substrate. Mesangial cell renin had characteristics similar to those of standard human renin; optimum enzymatic activity at pH 5.8, marked inhibition in the presence of two (monoclonal and polyclonal) human renin-specific antibodies and of SR 42128, a new potent statine-containing renin inhibitory peptide. The synthetic capability of the mesangial cells varied markedly with the original kidney (1-49 and 0.3-0.9 ng X h-1 X mg-1 for total renin in the medium and the cellular extract respectively). Renin was secreted mainly as inactive renin. Prostaglandin E2 (PGE2) and carba-prostaglandin I2 (PGI2) (a stable analogue) produced a dose-dependent (0.1-1.10 microM) increase in renin activity in both the cellular extract and the culture medium. Isoproterenol (200 microM) increased renin activity only in the medium. The effects of these agonists were more marked on inactive than on active renin. These results demonstrate that cultured human mesangial cells synthesize and release renin in a stable manner over a long period of culture, thus providing a useful tool for the in vitro study of renin secretion and its control.

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26

Pabel, Jörg, Mark Faust, Cornelia Prehn, Babette Wörlein, Lars Allmendinger, Georg Höfner, and Klaus T. Wanner. "Development of an (S)-1-{2-[Tris(4-methoxyphenyl)methoxy]ethyl}piperidine-3-carboxylic acid [(S)-SNAP-5114] Carba Analogue Inhibitor for Murine γ-Aminobutyric Acid Transporter Type 4." ChemMedChem 7, no. 7 (April 27, 2012): 1245–55. http://dx.doi.org/10.1002/cmdc.201200126.

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27

Perlman, M. B., S. K. Lo, and A. B. Malik. "Effect of prostacyclin on pulmonary vascular response to thrombin in awake sheep." Journal of Applied Physiology 60, no. 2 (February 1, 1986): 546–53. http://dx.doi.org/10.1152/jappl.1986.60.2.546.

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We determined the effects of infusion of prostacyclin (PGI2) and 6-alpha-carba-PGI2 (6-cPGI2), a stable PGI2 analogue, on pulmonary transvascular fluid and protein fluxes after intravascular coagulation induced by thrombin. Studies were made in control awake sheep prepared with lung lymph fistulas (n = 6) and in similarly prepared awake sheep pretreated with either 6-cPGI2 (n = 5) or PGI2 (n = 5). Both prostacyclin compounds (500 ng X kg-1 X min-1) were infused intravenously. All groups were challenged with 80 U/kg thrombin. Pulmonary arterial pressure (Ppa), pulmonary vascular resistance (PVR), pulmonary lymph flow (Qlym), lymph protein clearance (Qlym X lymph/plasma protein concentration ratio), and neutrophil and platelet counts were determined. In vitro tests assessed sheep neutrophil chemotaxis and chemiluminescence and platelet aggregation. In both 6-cPGI2 and PGI2 groups, the increases in Qlym after thrombin were less than those in the control group. The increase in lymph protein clearance in the 6-cPGI2 group was the same as that in control, whereas the increase in clearance in the PGI2 group was reduced. PVR and Ppa increased to a greater extent in the 6-cPGI2 group than in the control group, whereas the increases in PVR and Ppa were inhibited in the PGI2 group. Neutrophil and platelet counts decreased after thrombin in PGI2 and 6-cPGI2 groups, as they did in the control group. Neither 6-cPGI2 altered neutrophil chemotaxis induced by thrombin and chemiluminescence induced by opsonized zymosan. Both prostacyclin compounds inhibited platelet aggregation induced by ADP or thrombin.(ABSTRACT TRUNCATED AT 250 WORDS)

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28

Kishimba, M. A., and B. Zwanenburg. "Synthesis of carba-strigol analogues." Recueil des Travaux Chimiques des Pays-Bas 113, no. 1 (September 2, 2010): 21–28. http://dx.doi.org/10.1002/recl.19941130103.

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29

Ye, Bin, and Yu-Lin Wu. "Syntheses of carba-analogues of qinghaosu." Tetrahedron 45, no. 23 (January 1989): 7287–90. http://dx.doi.org/10.1016/s0040-4020(01)89189-4.

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30

Gómez-Coca, Raquel B., Larisa E. Kapinos, Antonı́n Holý, Rosario A. Vilaplana, Francisco González-Vı́lchez, and Helmut Sigel. "Intramolecular stacking interactions in ternary copper(II) complexes1 formed with 2,2′-bipyridine or 1,10-phenanthroline and 9-(4-phosphonobutyl)adenine (dPMEA), the carba relative of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA)." Journal of Inorganic Biochemistry 84, no. 1-2 (March 2001): 39–46. http://dx.doi.org/10.1016/s0162-0134(00)00194-x.

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31

Duchek, Jan, Mu-Hua Huang, and Andrea Vasella. "Towards stable di-carba analogues of guanofosfocins." Tetrahedron Letters 52, no. 23 (June 2011): 2940–42. http://dx.doi.org/10.1016/j.tetlet.2011.02.102.

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32

KISHIMBA, M. A., and B. ZWANENBURG. "ChemInform Abstract: Synthesis of Carba-Strigol Analogues." ChemInform 25, no. 24 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199424213.

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33

Lebl, Michal, Victor J. Hruby, Jiřina Slaninová, and Tomislav Barth. "Solid phase synthesis and biological activities of oxytocin carba analogues containing threonine in position 4." Collection of Czechoslovak Chemical Communications 50, no. 2 (1985): 418–27. http://dx.doi.org/10.1135/cccc19850418.

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Solis phase methodology was developed for the synthesis of carba-analogues of oxytocin. Two known compounds (deamino-1-carba-oxytocin (I) and deamino-6-carba-oxytocin (II)) and two new analogues ([4-threonine]deamino-1-carba-oxytocin (III) and [4-threonine]deamino-6-carba-oxytocin (IV)) were synthesized using different approaches. The latter two compounds were found to possess high biological activity in the rat uterotonic (in vitro and in vivo) and galactogogic (in vivo) assays.

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34

Seo, Kyung-Chang, Young-Geol Kwon, Dae-Hee Kim, In-Sook Jang, Jin-Won Cho, and Sung-Kee Chung. "Chemoenzymatic syntheses of carbasugar analogues of nucleoside diphosphate sugars: UDP-carba-Gal, UDP-carba-GlcNAc, UDP-carba-Glc, and GDP-carba-Man." Chemical Communications, no. 13 (2009): 1733. http://dx.doi.org/10.1039/b821058f.

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35

Mohar, Barbara, and Joze Kobe. "ChemInform Abstract: Chiral Synthons for carba-β-D-Ribonucleosides. Synthesis of carba-4-Deoxypyrazofurin and Isomeric carba-4-Deaza-oxoformycin Analogues." ChemInform 30, no. 38 (June 13, 2010): no. http://dx.doi.org/10.1002/chin.199938205.

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36

Buku, Angeliki, and Irving L. Schwartz. "Synthesis of carba vasopressin analogues by solid-phase cyclization." Journal of Protein Chemistry 4, no. 3 (June 1985): 163–70. http://dx.doi.org/10.1007/bf01025262.

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37

Jalife, Said, Martha Audiffred, Rafael Islas, Sigfrido Escalante, Sudip Pan, Pratim K. Chattaraj, and Gabriel Merino. "The inorganic analogues of carbo -benzene." Chemical Physics Letters 610-611 (August 2014): 209–12. http://dx.doi.org/10.1016/j.cplett.2014.07.038.

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38

Whelan, Amanda N., Jomana Elaridi, Roger J. Mulder, Andrea J. Robinson, and W. Roy Jackson. "Metal-catalysed tandem metathesis-hydrogenation reactions for the synthesis of carba analogues of cyclic peptides." Canadian Journal of Chemistry 83, no. 6-7 (June 1, 2005): 875–81. http://dx.doi.org/10.1139/v05-100.

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Dicarba cyclic peptide analogues of the cystine-containing octapeptides octreotide, lanreotide, and vapreotide, all known somatostatin analogues, have been synthesized via an on-resin homogeneous metal-catalysed sequence involving ruthenium-catalysed ring-closing metathesis followed by rhodium-catalysed hydrogenation.Key words: dicarba-analogues of cystine-containing peptides, octreotide, vapreotide, and lanreotide; tandem ring-closing metathesis and hydrogenation.

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39

Lebl, Michal, Tomislav Barth, Linda Servítová, Jiřina Slaninová, and Karel Jošt. "Oxytocin analogues with inhibitory properties, containing in position 2 a hydrophobic amino acid of D-configuration." Collection of Czechoslovak Chemical Communications 50, no. 1 (1985): 132–45. http://dx.doi.org/10.1135/cccc19850132.

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Ten analogues derived from oxytocin, deamino-oxytocin and deamino-carba-oxytocin were prepared which contained a D-amino acid in the position 2 of the parent system. The following D-amino acids were introduced: tyrosine, phenylalanine, p-methylphenylalanine, p-ethylphenylalanine and O-ethyltyrosine. Combination of two structural features which alone lead to strong inhibitors (a suitable D-amino acid in position 2 and a penicillamine moiety in position 1) did not enhance the inhibitory effect. Compounds containing D-tyrosine are weak agonists in the uterotonic assay; in case of 1-carba-analogues they can be converted into sulfoxides with low inhibitory activity. Analogues with D-phenylalanine substituted in the para-position are the most potent antagonists of the uterotonic effect of oxytocin (pA2 = 8.73) in vitro.

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40

Zhao, Yimin, Martina Michenfelder, and János Rétey. "Synthesis, characterization, and enzymic conversion of nonhydrolysable analogues of propionylcoenzyme A." Canadian Journal of Chemistry 72, no. 1 (January 1, 1994): 164–69. http://dx.doi.org/10.1139/v94-025.

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We describe the synthesis of three novel analogues of propionyl-coenzyme A, in which the sulfur atom has been replaced by methylene, ethylene, and thiomethylene, respectively. All three analogues, propionyl-dethia(carba)-CoA (1), propionyl-dethia(dicarba)-CoA (2), and S-(2-oxobutanyl)-CoA (3) were characterized by 1H and 31P NMR spectroscopy and FAB mass spectrometry. Propionyl-CoA–oxaloacetate transcarboxylase from Propionibacterium shermanii accepted the novel analogues as substrates and carboxylated them to the corresponding methylmalonyl-CoA analogues (4–6). The latter were further converted into the succinyl-CoA analogues by the coenzyme-B12-dependent methylmalonyl-CoA mutase from the same organism. The succinyl-CoA analogues, succinyl-dethia(carba)-CoA (7), succinyl-dethia(dicarba)-CoA (8), and 4-carboxy(2-oxobutanyl)-CoA (9) were obtained on a preparative scale and their Michaelis constants (Km) with methylmalonyl-CoA mutase were determined to be 0.136, 2.20, and 0.132 mM, respectively (Km for succinyl-CoA is 0.025 mM). The Vmax values for 7, 8, and 9 are 1.1, 0.013, and 0.0047 µmol min−1 U−1, respectively (Vmax for succinyl CoA is 1.0). The utility of the novel coenzyme A analogues in enzyme mechanistic studies is discussed.

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Gao, Qi, Marta Tontini, Giulia Brogioni, Alberto Nilo, Sara Filippini, Carole Harfouche, Laura Polito, et al. "Immunoactivity of Protein Conjugates of Carba Analogues fromNeisseria meningitidisA Capsular Polysaccharide." ACS Chemical Biology 8, no. 11 (September 19, 2013): 2561–67. http://dx.doi.org/10.1021/cb400463u.

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Hřebabecký, Hubert, and Antonín Holý. "Synthesis of Carba Analogues of 2'-Deoxy-4'-C-(hydroxymethyl)nucleosides." Collection of Czechoslovak Chemical Communications 64, no. 9 (1999): 1485–96. http://dx.doi.org/10.1135/cccc19991485.

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Racemic dimethyl 2-hydroxy-4-[5-methyl-2(1H),4(3H)-dioxopyrimidin-1-yl]- (7a and 8a) and dimethyl 4-(6-aminopurin-9-yl)-2-hydroxycyclopentane-1,1-dicarboxylates (7b and 8b) were prepared by addition of sodium salt of thymine and adenine, respectively, to dimethyl (Z)-(4-oxobut-2-en-1-yl)malonate (1). Reduction of the diesters with sodium borohydride in methanol in the presence of sulfuric acid gave corresponding racemic 2,2-bis(hydroxymethyl)-4-[5-methyl-2(1H),4(3H)-dioxopyrimidin-1-yl]- (14a and 15a), 4-(6-aminopurin- 9-yl)-2,2-bis(hydroxymethyl)cyclopentan-1-ol (14b and 15b), methyl (±)-cis-2-hydroxy- 1-hydroxymethyl-4-[5-methyl-2(1H),4(3H)-dioxopyrimidin-1-yl]- (13a), and methyl (±)-cis-4-(6-aminopurin-9-yl)-2-hydroxy-1-hydroxymethylcyclopentan-1-carboxylate (13b), respectively.

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Hlaváček, Jan, Renáta Marcová, Miloš Buděšínský, and Jiřina Slaninová. "1-Deamino-1(15)-carba and -Dicarba Analogues of Endothelin-1." Collection of Czechoslovak Chemical Communications 65, no. 3 (2000): 407–24. http://dx.doi.org/10.1135/cccc20000407.

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Sulfanyl-methylene and ethylene bridges were inserted into the molecule of endothelin-1 (ET-1) as other possible isosteric replacements of its outer disulfide linkage. The [1-deamino-1-carba]ET-1, [1-deamino-15-carba]ET-1 and [1-deamino-1,15-dicarba]ET-1 were synthesized either by a fragment condensation of protected cyclic pentadecapeptides with carboxy-terminal hexapeptides of the endothelin-1 sequence or by step-wise coupling on polymer support of the entire henicosapeptide sequences from carboxy-terminus. The analogues were devoid of uterotonic activity in comparison with the parent ET-1.

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Esposito, Annamaria, Maria Grazia Perino, and Maurizio Taddei. "Synthesis of Acyclic Carba-Nucleoside Phosphonates, Structural Analogues to Natural Deoxyribonucleotides." European Journal of Organic Chemistry 1999, no. 4 (April 1999): 931–36. http://dx.doi.org/10.1002/(sici)1099-0690(199904)1999:4<931::aid-ejoc931>3.0.co;2-r.

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Furenes, Eline Bredal, Jaco Luijendijk, Jon Efskind, and Kjell Undheim. "Synthesis of Benzene‐1‐Alanine‐3‐Glycine as Carba Analogues of Cystine." Synthetic Communications 35, no. 2 (January 2005): 193–200. http://dx.doi.org/10.1081/scc-200048407.

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Carpintero, Mercedes, Carlos Jaramillo, and Alfonso Fernandez-Mayorales. "ChemInform Abstract: Stereoselective Synthesis of carba- and C-Glycosyl Analogues of Fucopyranosides." ChemInform 31, no. 24 (June 8, 2010): no. http://dx.doi.org/10.1002/chin.200024202.

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Ramella, Daniela, Laura Polito, Stefania Mazzini, Silvia Ronchi, Leonardo Scaglioni, Marcello Marelli, and Luigi Lay. "A Strategy for Multivalent Presentation of Carba Analogues fromN. meningitidisA Capsular Polysaccharide." European Journal of Organic Chemistry 2014, no. 27 (August 20, 2014): 5915–24. http://dx.doi.org/10.1002/ejoc.201402701.

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TOLSTIKOV, G. A., M. S. MIFTAKHOV, F. A. VALEEV, and A. A. GAREEV. "ChemInform Abstract: Enantiomeric Carba Analogues of Prostaglandin endo-Peroxide: A Key Synthon." ChemInform 22, no. 18 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199118287.

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Wimmer, Zdeněk, Ludvík Streinz, and Miroslav Romaňuk. "Preparation of carbamate derivatives of 2-(4-hydroxybenzyl)-1-cyclohexanone with a juvenoid activity." Collection of Czechoslovak Chemical Communications 50, no. 11 (1985): 2453–56. http://dx.doi.org/10.1135/cccc19852453.

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The synthesis of four carbamate derivatives of 2-(4-hydroxybenzyl)-1-cyclohexanone displaying a juvenilizing effect in insects is described. The substances prepared have a greater stability and activity than their carba-analogues prepared earlier.

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Lozynskyi, Oleg, Cécile Barthes, Arnaud Rives, Valérie Maraval, Zoia Voitenko, and Remi Chauvin. "En route to a dianilinyl-substituted carbo-cyclohexadiene with promising electrical properties." French-Ukrainian Journal of Chemistry 3, no. 1 (2015): 46–52. http://dx.doi.org/10.17721/fujcv3i1p46-52.

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The macro-aromatic carbo-benzene core para-disubstituted by 4-anilinyl groups is known to be an efficient single-molecule conductor, exhibiting a conductance of 106 nS measured by the scanning tunneling microscopy-break junction technique. The linear carbo-butadiene analogue bearing the same anilinyl substituents was found to be less efficient, with a conductance of 2.7 nS. The reason of this difference could be elucidated through the study of the charge transport properties of a cyclically locked carbo-butadiene core in a carbo-cyclohexadiene derivative. In this paper, advances in the synthesis of this challenging dianilinyl-substituted carbo-cyclohexadiene are presented.

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