Preparation and Determination of Sodiumhydrogen S-(2-aminoethyl) Phosphorothioate (Sodiumhydrogen Cysteamine-S-phosphate).

Åkerfeldt, Stig; Berglund, Curt; Meier, Hans; Hedén, C.‐G.; Malmgren, B.; Palmstierna, H.

doi:10.3891/acta.chem.scand.13-1479

Cited by 38 publications

(8 citation statements)

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“…The Department of Chemistry, The Ohio State University, Columbus,Ohio 4SSlO Received February 11,1966 Procedures have been developed for the mono-and dialkylation of p-keto sulfoxides. Reductive cleavage of these alkylated p-keto sulfoxides with aluminum amalgam provides an attractive synthetic route to a wide variety of ketones.…”

Section: The Alkylation Of P-keto Sulfoxides a General Route To Ketonesmentioning

confidence: 99%

2-Amino-Δ²-thiazolines from Aminoethyl Thiosulfates. The Mass Spectra of 2-Amino-Δ²-thiazolines and Related Compounds

Klayman¹,

Milne²

1966

J. Org. Chem.

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Compd I11a I Maximum, m p (log e) erlenmeyer flask (oil bath) for 1 hr at 170". During this heating the product was slowly precipitated as a tan crystalline solid. The reaction mixture which was almost completely solid was cooled and then treated with boiling ethyl acetate. Filtration gave 2.5 g (50%) of pure benzo[c]quinolizinium chloride IIIa (X = Cl), mp 247-249'.Recrystallization from 95% ethanolethyl acetate produced no change in melting point. Evaporation of the ethyl acetate filtrate gave trans-2'-chloro-2-stilbazole (Ia) which recrystallized from ligroin (bp 60-90') to yield 2.0 g When the purified cis isomer IIa (X = C1) was cyclized by heating at 170" for 1 hr, a 557' yield of the quinolizinium salt IIIa (X = Cl), based on cis isomer initially used, was obtained. Method B. Benzo[cjquinolizinium Perchlorate (IIIa, X =The attack of cyanide ion on primary and secondary aminoethyl thiosulfates yields 2-amino-A*-thiazolines. 2-Aminoethyl 2-aminoethanethiolsulfonate and 2-aminoethyl 2-aminoethanethiolsulfinate on treatment with cyanide also yield 2-amino-A2-thiazoline (I). The mass spectra of I, three isomeric methyl-2-amino-A~-thiazolines, 2-imino-3-amidinothiazolidine, and 2-amino-5,6-dihydro-4H-lJ3-thiazine, made from thiosulfates by the above method, as well as 2-methylamino-A2-thiazoline and 2-amino-A2-selenazoline, have been analyzed and found to support the assigned structures. A previously undescribed variation of the McLafferty rearrangement is reported.

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Section: The Alkylation Of P-keto Sulfoxides a General Route To Ketonesmentioning

confidence: 99%

2-Amino-Δ²-thiazolines from Aminoethyl Thiosulfates. The Mass Spectra of 2-Amino-Δ²-thiazolines and Related Compounds

Klayman¹,

Milne²

1966

J. Org. Chem.

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“…From 1959From until 1973 Walter Reed Army Institute of Research had synthesized 4000 compounds and screened them in mice [9] . The most significant contribution of the institute was through the R&D of WR-2721 (S-2-3-aminopropylamino) ethylphosphorothioic acid, and many related phosphorothioates, which were first synthesized by Akerfeldt in 1959 as RAs [10] . This achievement has continued whereby WR-2721 then being introduced to cancer clinical trials to study protection against normal tissue damage caused by radiation therapy (radiotherapy) [11] .…”

Section: Introductionmentioning

confidence: 99%

Research and Development of Radioprotective Agents: A Mini-Review

Saaya

Katsube

Xie

et al. 2017

International Journal of Radiology

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The research and development (R&D) of radioprotective agents (RAs) have been conducting since seven decades ago, and the safety and protection against undesirable effects of ionizing radiation (IR) has become an important issue especially for the benefit of patients receiving the radiotherapy, in addition to the applications in nuclear industry, military, outer space exploration and accidental exposures. Although the technology advancement makes the radiotherapy a promising better treatment by maximizing the effect of IR to the cancer cells, there are still needs for improvement in minimizing the toxicity to the normal cells. Aiming at providing the new researchers in the radiation protection field with an overall view for R&D of the RAs, this mini-review elucidates in brief a general understanding of the IR and its effects on the cell, the concepts of radiotherapy and therapeutic ratio, the categories of RAs and their mechanisms, and discusses on the strategies and challenge for R&D of the RAs.

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“…Much of the information generated-relating structure, toxicity, and radiation protective ability, for over 4ooo compounds-was compiled by Sweeney (1979). Perhaps the most significant development from that program was the synthesis and early testing of the phosphorothioate class of radiation protective compounds (Akerfeldt, 1959(Akerfeldt, , 1963. This class of protectors is the most widely studied and provides the best protection to date.…”

Section: Historical Summarymentioning

confidence: 99%

Radiation Protectors: the Unexpected Benefits

Grdina

Sigdestad

1989

Drug Metabolism Reviews

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Preparation and Determination of Sodiumhydrogen S-(2-aminoethyl) Phosphorothioate (Sodiumhydrogen Cysteamine-S-phosphate).

Cited by 38 publications

References 0 publications

2-Amino-Δ²-thiazolines from Aminoethyl Thiosulfates. The Mass Spectra of 2-Amino-Δ²-thiazolines and Related Compounds

2-Amino-Δ²-thiazolines from Aminoethyl Thiosulfates. The Mass Spectra of 2-Amino-Δ²-thiazolines and Related Compounds

Research and Development of Radioprotective Agents: A Mini-Review

Radiation Protectors: the Unexpected Benefits

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Preparation and Determination of Sodiumhydrogen S-(2-aminoethyl) Phosphorothioate (Sodiumhydrogen Cysteamine-S-phosphate).

Cited by 38 publications

References 0 publications

2-Amino-Δ2-thiazolines from Aminoethyl Thiosulfates. The Mass Spectra of 2-Amino-Δ2-thiazolines and Related Compounds

2-Amino-Δ2-thiazolines from Aminoethyl Thiosulfates. The Mass Spectra of 2-Amino-Δ2-thiazolines and Related Compounds

Research and Development of Radioprotective Agents: A Mini-Review

Radiation Protectors: the Unexpected Benefits

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Product

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2-Amino-Δ²-thiazolines from Aminoethyl Thiosulfates. The Mass Spectra of 2-Amino-Δ²-thiazolines and Related Compounds

2-Amino-Δ²-thiazolines from Aminoethyl Thiosulfates. The Mass Spectra of 2-Amino-Δ²-thiazolines and Related Compounds