Isosterism and bioisosterism in drug design.

In every scientific undertaking that is to break new ground, one has to have a goal, a working hypothesis, or a leading idea or fact. This will encourage research and help in the pursuit of a worth-while objective, be it the enrichment of knowledge or the elaboration of a practical purpose. A medicinal scientist who hopes to find a new biologically active drug will have to be guided by such considerations.

[1]  G. R. Brown,et al.  Receptor binding sites of hypoglycemic sulfonylureas and related [(acylamino)alkyl]benzoic acids. , 1984, Journal of medicinal chemistry.

[2]  H. Schaeffer,et al.  Novel substrate of adenosine deaminase. , 1971, Journal of medicinal chemistry.

[3]  C. Hansch,et al.  On the structure of medicinal chemistry. , 1976, Journal of medicinal chemistry.

[4]  A. Leo,et al.  Substituent constants for correlation analysis. , 1977, Journal of medicinal chemistry.

[5]  E. Gravela,et al.  In the search for new anticancer drugs. 13. Phosphonic and phosphinic analogues of ornithine. , 1985, Journal of medicinal chemistry.

[6]  D. J. Bauer,et al.  9-(2-Hydroxyethoxymethyl)guanine activity against viruses of the herpes group , 1978, Nature.

[7]  R. S. Mulliken.  Bonding Power of Electrons and Theory of Valence. , 1931 .

[8]  W. B. Wright,et al.  Thromboxane synthetase inhibitors and antihypertensive agents. 1. N-[(1H-imidazol-1-yl)alkyl]aryl amides and N-[(1H-1,2,4-triazol-1-yl)alkyl]aryl amides. , 1986, Journal of medicinal chemistry.

[9]  Y. Kondo,et al.  Antimalarial phenanthrene amino alcohols.1. Fluorine-containing 3- and 6-substituted 9-phenanthrenemethanols. , 1971, Journal of medicinal chemistry.

[10]  M. Hropot,et al.  5-sulfamoylorthanilic acids, a sulfonamide series with salidiuretic activity. , 1983, Journal of medicinal chemistry.

[11]  L. Small,et al.  Amino Alcohols Derived from Carbazole. II1 , 1938 .

[12]  A. Burger,et al.  D-Glucopyranose 6-Deoxy-6-phosphonic Acid , 1956 .

[13]  H. Brown,et al.  The Structure and Toxicity of DDT Insecticides , 1953 .

[14]  G. Cooper,et al.  META-AMINO PARA-HYDROXY PHENYL ARSINE OXIDE AS AN ANTISYPHILITIC AGENT. , 1932, Science.

[15]  C. Hansch,et al.  A NEW SUBSTITUENT CONSTANT, PI, DERIVED FROM PARTITION COEFFICIENTS , 1964 .

[16]  R. R. Bower,et al.  Synthesis and anti-herpes simplex activity of analogues of phosphonoacetic acid. , 1977, Journal of medicinal chemistry.

[17]  D. Miller,et al.  Dopaminergic agonists: comparative actions of amine and sulfonium analogues of dopamine. , 1984, Journal of medicinal chemistry.

[18]  C. Hansch,et al.  p-σ-π Analysis. A Method for the Correlation of Biological Activity and Chemical Structure , 1964 .

[19]  Orville H. Miller,et al.  The Synthesis of Several Dialkylmalonylguanidines with a Preliminary note on their Pharmacology , 1941 .

[20]  L. Overby,et al.  ANTIVIRAL POTENTIAL OF PHOSPHONOACETIC ACID , 1977, Annals of the New York Academy of Sciences.

[21]  A. Leo,et al.  Substituent constants for correlation analysis in chemistry and biology , 1979 .

[22]  K. Florey,et al.  Analytical profiles of drug substances , 1972 .

[23]  A. Burger,et al.  Antimalarials. II. Alpha-(2-piperidyl)-and alpha-(2-pyridyl)-2-trifluoromethyl-4-quinolinemethanols. , 1968, Journal of medicinal chemistry.

[24]  A. C. Brown,et al.  V.—On the Connection between Chemical Constitution and Physiological Action. Part. I.—On the Physiological Action of the Salts of the Ammonium Bases, derived from Strychnia, Brucia, Thebaia, Codeia, Morphia, and Nicotia , 1870, Transactions of the Royal Society of Edinburgh.

[25]  W. Carter.  Selective Inhibitors Of Viral Functions , 1973 .

[26]  R. Kuhn,et al.  4.4′-Diamino-benzophenon und andere schwefelfreie Verbindungen mit Sulfonamidwirkung , 1942 .

[27]  J. C. Emmett,et al.  Thyroid hormone analogues. Synthesis of 3'-substituted 3,5-diiodo-L-thyronines and quantitative structure-activity studies of in vitro and in vivo thyromimetic activities in rat liver and heart. , 1988, Journal of medicinal chemistry.

[28]  J. Büchi,et al.  Synthese und analgetische Wirkung einiger 1‐Methyl‐4‐phenyl‐piperidin‐(4)‐alkylsulfone. 1. Mitteilung , 1952 .

[29]  W J Dunn,et al.  Linear relationships between lipophilic character and biological activity of drugs. , 1972, Journal of pharmaceutical sciences.

[30]  J. Bruin,et al.  Synthesis of 8-azaprostaglandin E1 and E2 , 1976 .

[31]  H. Schaeffer,et al.  Selectivity of action of an antiherpetic agent, 9-(2-hydroxyethoxymethyl) guanine. , 1977, Proceedings of the National Academy of Sciences of the United States of America.

[32]  H. Erlenmeyer,et al.  Über Pseudoatome und isostere Verbindungen. Ein Vergleich der Gruppen N2 und CO , 1933 .

[33]  Y. Martin,et al.  Quantitative drug design: A critical introduction , 1978 .

[34]  R. K. Robins,et al.  Broad-Spectrum Antiviral Activity of Virazole: 1-f8- D-Ribofuranosyl- 1,2,4-triazole- 3-carboxamide , 1972, Science.

[35]  W. J. Novick,et al.  [(3-aryl-1,2-benzisoxazol-6-yl)oxy]acetic acids. A new diuretic series. , 1982, Journal of medicinal chemistry.

[36]  J. Kraus,et al.  Isosterism and molecular modification in drug design: tetrazole analogue of GABA: effects on enzymes of the gamma-aminobutyrate system. , 1983, Pharmacological research communications.

[37]  G. Blackburn,et al.  Isopolar vs Isosteric Phosphonate Analogues of Nucleotides , 1985 .

[38]  R. Shepherd,et al.  Sulfanilamidopyrimidines. I. 4-Sulfanilamidopyrimidines by Heterocyclic Nucleophilic Displacements , 1961 .

[39]  F. Hauser,et al.  10-oxa-11-desoxy-prostaglandins , 1974 .

[40]  J. Druey,et al.  Heilmittelchemische Untersuchungen in der heterocyclischen Reihe. Mitteilung. Pyrazolo‐(3,4‐d)‐pyrimidine , 1956 .

[41]  E. Hessler.  An efficient synthesis of 1-beta-D-arabinofuranosylcytosine. , 1976, The Journal of organic chemistry.

[42]  H. Köhler,et al.  Dicyanmethanido‐ und Cyanamido‐oxoanionen. Untersuchungen zum sauerstoffanalogen Charakter der C(CN)2‐ und NCN‐Gruppen , 1970 .

[43]  R. Schinazi,et al.  Synthesis and antiviral activity of various 3'-azido analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1, HTLV-III/LAV). , 1988, Journal of medicinal chemistry.

[44]  R. C. Elderfield,et al.  STUDIES IN THE PYRIDINE SERIES. II. SYNTHESIS OF 2-METHYL-3-(β-HYDROXYETHYL)PYRIDINE AND OF THE PYRIDINE ANALOG OF THIAMINE (VITAMIN B1) , 1941 .

[45]  J. T. Litchfield,et al.  The sulfonamides and allied compounds , 1948 .

[46]  M. Wolff,et al.  Antibody-directed drug discovery , 1990, Nature.

[47]  P. Goldman,et al.  Nitrosoimidazoles: highly bactericidal analogues of 5-nitroimidazole drugs. , 1988, Journal of medicinal chemistry.

[48]  C. Ho,et al.  Synthesis and in vitro antimicrobial activity of 5-substituted 2H-1,3,5-thiadiazine-2,4(3H)-diones. , 1982, Journal of medicinal chemistry.

[49]  H. Erlenmeyer,et al.  Zur Kenntnis der Eigenschaften isosterer und strukturähnlicher Verbindungen VII. Über die Darstellung des 4‐Oxy‐benzthiazol , 1938 .

[50]  G. Spiteller,et al.  Zweitsynthese des 6-Sulfanilamido-2,4-dimethoxy-pyrimidins und Synthese des 6-Sulfanilamido-2-methoxy-4,5-dimethylpyrimidins 6. Mitt. über neue N 1 -substituierte Sulfonamide , 1961 .

[51]  C. Nathan,et al.  Inhibition of macrophage and endothelial cell nitric oxide synthase by diphenyleneiodonium and its analogs 1 , 1991, FASEB journal : official publication of the Federation of American Societies for Experimental Biology.

[52]  H. Erlenmeyer,et al.  Beiträge zum Problem der Ähnlichkeit bei Komplexverbindungen. Metallionen und biologische Wirkung, 19. Mitteilung , 1954 .

[53]  J. Burckhalter.  Molecular Modification in Drug Design , 1966 .

[54]  J. Lockhart,et al.  784. The denitration of nitroguanidines in strong acids. Part II. Absorption spectra and pKa values of certain nitroguanidines , 1958 .

[55]  D. L. Tabern,et al.  Sulfur-Containing Barbiturate Hypnotics , 1935 .

[56]  K. Wallenfels,et al.  The Analogy between O and C(CN)2 , 1976 .

[57]  R. R. Burtner,et al.  Antispasmodics. I. Basic Esters of Some Arylacetic Acids1 , 1943 .

[58]  R. Curley,et al.  Synthesis of aminomethyl-substituted cyclic imide derivatives for evaluation as anticonvulsants. , 1983, Journal of medicinal chemistry.

[59]  D. Ward,et al.  Nucleoside analogs with antiviral activity. , 1976, Biochemical pharmacology.

[60]  R. Robinson,et al.  355. β-Phenylfurylethylamine and analogous derivatives of thiophen and pyrrole , 1939 .

[61]  N. B. Eddy,et al.  Theories of general anesthesia. , 1950 .

[62]  R. Sidwell,et al.  Synthesis and antiviral and antimicrobial activity of certain 1-beta-D-ribofuranosyl-4,5-disubstituted imidazoles. , 1976, Journal of medicinal chemistry.

[63]  C. Harris,et al.  The synthesis and biological activities of some 12-Aza-prostaglandin analogues , 1978 .

[64]  D. Cram,et al.  The design of molecular hosts, guests, and their complexes , 1988, Science.

[65]  E. Cragoe,et al.  Prostaglandin isosteres. 1. (8-Aza-, 8,10-diaza-, and 8-aza-11-thia)-9-oxoprostanoic acids and their derivatives. , 1977, Journal of medicinal chemistry.

[66]  H. Lewis,et al.  NUCLEOSIDES. I. A NEW SYNTHESIS OF 1-BETA-D-ARABINOFURANOSYL PYRIMIDINE NUCLEOSIDES. , 1965, The Journal of organic chemistry.

[67]  L. D. Freedman,et al.  The Preparation And Properties Of Phosphonic Acids , 1957 .

[68]  A. L. Morrison,et al.  303. Synthetic analgesics. Part VI. The synthesis of ketobemidone , 1950 .

[69]  R. I. Thrift.  Derivatives of 2-aminoetetralin , 1967 .

[70]  T. Eggelte,et al.  Synthesis of 9,11-dideoxy-9a-homoprostaglandins† , 1977 .

[71]  L. Overby,et al.  Inhibition of DNA Polymerase from Herpes Simplex Virus-Infected Wi-38 Cells by Phosphonoacetic Acid , 1975, Journal of virology.

[72]  E. Mack,et al.  THE ANGLE BETWEEN THE OXYGEN BONDS BY THE COLLISION AREA METHOD , 1932 .

[73]  P. Polster,et al.  The effect of cardiac muscle of two drugs related to amiodarone, L8040 and L8462. , 1974, European journal of pharmacology.

[74]  Beziehungen zwischen der Struktur der Antigene und der Spezifität der Antikörper , 1933 .

[75]  D. K. Phillips,et al.  Bulky amine analogues of ketoprofen: potent antiinflammatory agents. , 1984, Journal of medicinal chemistry.

[76]  F. Westheimer.  Why nature chose phosphates. , 1987, Science.

[77]  C. Le.  Curariform activity and chemical structure. , 1948 .

[78]  W. Steinkopf,et al.  XVIII. Die Synthese des Thiophen‐isologen des Atropins , 1924 .

[79]  D. B. Ellis,et al.  Synthesis and neuroleptic activity of 3-(1-substituted-4-piperidinyl)-1,2-benzisoxazoles. , 1985, Journal of medicinal chemistry.

[80]  D. Green,et al.  On the dopamine‐like action of apomorphine , 1971, The Journal of pharmacy and pharmacology.

[81]  P. Kovacic,et al.  Spirobarbituric Acids Containing a Six-membered Carbocyclic Ring , 1949 .

[82]  J. Clemens,et al.  Bicyclic and tricyclic ergoline partial structures. Rigid 3-(2-aminoethyl)pyrroles and 3- and 4-(2-aminoethyl)pyrazoles as dopamine agonists. , 1980, Journal of medicinal chemistry.

[83]  J. M. Weaver,et al.  Mesoionic pyridazine ribonucleosides. A novel biologically active nucleoside metabolite. , 1984, Journal of medicinal chemistry.

[84]  R. Roblin,et al.  Studies in Chemotherapy. VIII. Methionine and Purine Antagonists and their Relation to the Sulfonamides1 , 1945 .

[85]  R. G. Schmitt,et al.  Spectrophotometrically Determined Ionization Constants of Derivatives of Symmetric Triazine. , 1961 .

[86]  B. Branchaud,et al.  Synthesis of 11-deoxy-8-azaprostaglandin E1. , 1977, The Journal of organic chemistry.

[87]  R. Foster,et al.  Studies in analgesia; piperidine derivatives with morphine-like activity. , 1947, The Journal of pharmacology and experimental therapeutics.

[88]  E. Gravela,et al.  IN SEARCH OF NEW ANTICANCER DRUGS. 13. PHOSPHONIC AND PHOSPHINIC ANALOGS OF ORNITHINE , 1985 .

[89]  Aalt Bast,et al.  Comprehensive medicinal chemistry , 1991 .

[90]  G. Hitchings,et al.  THE EFFECTS OF PYRIMIDINES ON THE GROWTH OF LACTOBACILLUS CASEI. , 1945, Science.

[91]  H. Blank,et al.  Inhibition of Growth of Hair by Mimosine , 1962, Nature.

[92]  S H Unger,et al.  "Aromatic" substituent constants for structure-activity correlations. , 1973, Journal of medicinal chemistry.

[93]  M. Soodak,et al.  Studies on Oxythiamine , 1944 .

[94]  C. Heidelberger,et al.  THE SYNTHESIS OF 5-FLUOROPYRIMIDINES , 1957 .

[95]  A. Korolkovas.  Drug Action. (Book Reviews: Essentials of Molecular Pharmacology. Background for Drug Design) , 1970 .

[96]  J. Mao,et al.  Mode of inhibition of herpes simplex virus DNA polymerase by phosphonoacetate. , 1975, Biochemistry.

[97]  D. Woolley,et al.  SELECTIVE REVERSIBLE INHIBITION OF MICROBIAL GROWTH WITH PYRITHIAMINE , 1943, The Journal of experimental medicine.

[98]  P. Anderson,et al.  N-(1,3,4,6,7,12b-hexahydro-2H-benzo[b]furo[2,3-a]quinolizin -2-yl)-N- methyl-2-hydroxyethane-sulfonamide: a potent and selective alpha 2-adrenoceptor antagonist. , 1985, Journal of medicinal chemistry.

[99]  H. Erlenmeyer,et al.  Zusammenhänge zwischen Konstitution und Wirkung bei Pyrazolonderivaten , 1935 .

[100]  S. Archer,et al.  The preparation and properties of some benzohydryl sulfones. , 1948, Journal of the American Chemical Society.

[101]  Molecular complexes of thyroid hormone tyrosyl rings with aromatic donors. Possible relationship to receptor protein interactions. , 1988, Journal of medicinal chemistry.

[102]  J. Rokach,et al.  Kojic amine--a novel gamma-aminobutyric acid analogue. , 1979, Journal of medicinal chemistry.

[103]  I. M. Klotz,et al.  The antibacterial activity of p-aminobenzenephosphonous acid. , 1947, Journal of the American Chemical Society.

[104]  D. Ledbetter,et al.  Chromosome 17 deletions and p53 gene mutations in colorectal carcinomas. , 1989, Science.

[105]  G. Barger,et al.  399. Synthesis of β-2-thienylalanine and of β-2-thienylethylamine , 1938 .

[106]  Carl-Eric Kaiser,et al.  Dopamine receptors: Functions, subtypes and emerging concepts , 1985, Medicinal research reviews.

[107]  F. Bossert,et al.  [Dihydropyridines, a new group of strongly effective coronary therapeutic agents]. , 1971, Die Naturwissenschaften.

[108]  D. Walters,et al.  Potential antisecretory antidiarrheals. 1. Alpha 2-adrenergic aromatic aminoguanidine hydrazones. , 1988, Journal of medicinal chemistry.

[109]  A. Burger,et al.  A Guide to the Chemical Basis of Drug Design , 1983 .

[110]  G. B. Brown,et al.  THE INHIBITION OF THE GROWTH OF YEAST BY THIENYLALANINE , 1945 .

[111]  W. Steinkopf,et al.  Studien in der Thiophenreihe XVII. Die Darstellung des Thiophenisologen des Cocains , 1924 .

[112]  G. M. Drew,et al.  Peripheral dopamine receptor subtypes- a closer look , 1985 .

[113]  J. Monn,et al.  Conformational preference for the binding of biaryl substrates and inhibitors to the active site of phenylethanolamine N-methyltransferase. , 1988, Journal of medicinal chemistry.

[114]  T. C. Bruice,et al.  A correlation of thyroxine-like activity and chemical structure. , 1956, Archives of biochemistry and biophysics.

[115]  B. Belleau,et al.  Synthesis and crystal structure of 17-deaza-17-methyl thionium isomorphinan (isosulforphanol) perchlorate, an isostere of the opiate isolevorphanol , 1985 .

[116]  A. Burger,et al.  3-Iodo-, 3,3'-Diiodo- and 3,3'-Diiodo-5-bromothyronine1 , 1956 .

[117]  A. Patchett,et al.  Inhibitors of glycolic acid oxidase. 4-substituted 2,4-dioxobutanoic acid derivatives. , 1983, Journal of medicinal chemistry.

[118]  E. Huang.  Human cytomegalovirus. IV. Specific inhibition of virus-induced DNA polymerase activity and viral DNA replication by phosphonoacetic acid , 1975, Journal of virology.

[119]  H. Gilman,et al.  THE CORRELATION OF SOME AROMATIC TYPES WITH PHYSIOLOGICAL ACTION. LOCAL ANESTHETICS CONTAINING THE FURAN, THIOPHENE AND PYRROLE NUCLEI1 , 1925 .

[120]  Y. Martin,et al.  A practitioner's perspective of the role of quantitative structure-activity analysis in medicinal chemistry. , 1981, Journal of medicinal chemistry.

[121]  V. Goldschmidt.  Krystallbau und chemische Zusammensetzung , 1927 .

[122]  D. Calne,et al.  (+)-4-PROPYL-9-HYDROXYNAPHTHOXAZINE (PHNO), A NEW DOPAMINOMIMETIC, IN TREATMENT OF PARKINSONISM , 1985, The Lancet.

[123]  C. Broquet,et al.  Structure-activity relationship in PAF-acether. 4. Synthesis and biological activities of carboxylate isosteres. , 1988, Journal of medicinal chemistry.

[124]  R. A. Johnson,et al.  Thromboxane A2 synthase inhibitors. 5-(3-Pyridylmethyl)benzofuran-2-carboxylic acids. , 1986, Journal of medicinal chemistry.

[125]  D. Woolley,et al.  PRODUCTION OF THIAMINE DEFICIENCY DISEASE BY THE FEEDING OF A PYRIDINE ANALOGUE OF THIAMINE , 1943 .

[126]  I. Page,et al.  Nature of the hypotensive action of a thiophanium derivative (Ro 2-2222) in dogs. , 1952, The Journal of pharmacology and experimental therapeutics.

[127]  A. R. Patel,et al.  Antimalarials. 7. Bis(trifluoromethyl)-.alpha.-(2-piperidyl)-4-quinolinemethanols , 1971 .

[128]  S. Free,et al.  A MATHEMATICAL CONTRIBUTION TO STRUCTURE-ACTIVITY STUDIES. , 1964, Journal of medicinal chemistry.

[129]  T. Fujita,et al.  Structure-activity study of phenethylamines as substrates of biosynthetic enzymes of sympathetic transmitters. , 1971, Journal of medicinal chemistry.

[130]  M. Goodman.  Peptide homologs, isosteres, and isomers: A general approach to structure–activity relationships , 1985, Biopolymers.

[131]  C. Hansch,et al.  The use of triazine inhibitors in mapping the active site region of Lactobacillus casei dihydrofolate reductase. , 1979, Archives of biochemistry and biophysics.

[132]  W. Hieber,et al.  Über Metallcarbonyle. VII. Über die Raumbeanspruchung des Kohlenoxyds in seinen Metallsalz‐Verbindungen und in den Metallcarbonylen , 1930 .

[133]  C. Thornber,et al.  Isosterism and molecular modification in drug design , 1979 .

[134]  J. Katzenellenbogen,et al.  Acylamino boronic acids and difluoroborane analogues of amino acids: potent inhibitors of chymotrypsin and elastase. , 1985, Journal of medicinal chemistry.

[135]  C. Suter.  Relationships between the Structure and the Bactericidal Properties of Phenols. , 1941 .

[136]  E. De Clercq,et al.  (S)-9-(2,3-Dihydroxypropyl)adenine: An Aliphatic Nucleoside Analog with Broad-Spectrum Antiviral Activity , 1978, Science.

[137]  I. Langmuir.  ISOMORPHISM, ISOSTERISM AND COVALENCE. , 1919 .

[138]  J. B. Farmer,et al.  α-[(t-Butylamino)methyl]-4-hydroxy-m-xylene-α1, α3-diol (AH.3365): a Selective β-Adrenergic Stimulant , 1968, Nature.

[139]  M. Wolff,et al.  Apparent bioisosteric replacement of--S--by NCN: synthesis of N--cyano-2-aza-A-nor-5alpha-androstan-17beta-ol acetate, an aza steroid androgen. , 1979, Journal of medicinal chemistry.

[140]  J. L. Barker,et al.  Salicylate: A Structure-Activity Study of its Effects on Membrane Permeability , 1972, Science.

[141]  L. Birckenbach,et al.  Über die Cyan-Abkömmlinge der flüchtigen Hydride , 1930 .

[142]  G. Hitchings,et al.  Metabolic studies of allopurinol, an inhibitor of xanthine oxidase. , 1966, Biochemical pharmacology.

[143]  L. Birckenbach,et al.  Über Pseudohalogene (I) , 1925 .

[144]  J. Jones,et al.  11,12-secoprostaglandins. 4. 7-(N-alkylmethanesulfonamido) heptanoic acids. , 1977, Journal of medicinal chemistry.

[145]  A. Leo,et al.  Partition coefficients and their uses , 1971 .

[146]  R. K. Robins.  Potential Purine Antagonists. I. Synthesis of Some 4,6-Substituted Pyrazolo [3,4-d] pyrimidines1 , 1956 .

[147]  C. Triggle,et al.  Chemical pharmacology of the synapse , 1976 .

[148]  K. Miescher,et al.  Über eine neue Synthese morphinähnlich wirkender 4-Phenylpiperidin-4-alkylketone und verwandter Verbindungen , 1949 .

[149]  D W Barry,et al.  3'-Azido-3'-deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro. , 1985, Proceedings of the National Academy of Sciences of the United States of America.

[150]  H. van de Waterbeemd,et al.  Theoretical conformational studies on some dopamine antagonistic benzamide drugs: 3-pyrrolidyl- and 4-piperidyl derivatives. , 1983, Journal of medicinal chemistry.

[151]  J. Black,et al.  Potential histamine H2-receptor antagonists. 2. N-alpha-Guanylhistamine. , 1975, Journal of medicinal chemistry.

[152]  L. Birckenbach,et al.  Über Pseudohalogene, IV.: Die Hydrolysen-Konstanten des Brom-tricyanmethyls und des Chlor-, Brom- und Jod-trinitromethyls , 1929 .

[153]  G. W. Wheland,et al.  Resonance in Organic Chemistry , 1956 .

[154]  G. Diana,et al.  Synthesis of some phosphonates with antiherpetic activity. , 1984, Journal of medicinal chemistry.