Abstract
An improved synthetic scheme for (5Z)-7-{3-endo-[(benzenesulfonamido)-bicyclo[2.2.1]heptyl}-hept-5-enoic acid (S145) and its analogs has been designed. The procedure involves direct sulfonylation of 2-allyl-3-aminobicyclo[2.2.1]heptane intermediate followed by ozonolysis and addition of a C5 carboxyl unit. The yield of the final product was significantly improved. (5Z)-7-{3-endo-[(4-iodobenzensulfonamido)-bicyclo [2.2.1]heptyl}hept-5-enoic acid (HS-145) and (5Z)-7-{3-endo-[(4-hydroxy-benzensulfonamido)-bicyclo [2.2.1]heptyl}hept-5-enoic acid (HS-145) were synthesized directly without any protection and deprotection steps. [125I](5Z)-7-{3-endo-[(4-iodobenzensulfonamido)- bicyclo[2.2.1]heptyl}hept-5-enoic acid ([125I]HS-145) was prepared from IS-145 through an organotin intermediate and [125I]sodium iodide with high specific radioactivity and good recovery of radioactivity. [125I](5Z)-7-{3-endo-[(4-hydroxy 3-iodo-benzensulfonamido)-bicyclo[2.2.1]-heptyl}hept-5-enoic acid ([125I]HS-145) was prepared by direct iodination with sodium iodide using a modified chloramine-T method. Both [125]HS-145 and [125I]HS-145 were found to be valuable radioligands for studying thromboxane A2 (TXA2) receptor.
| Original language | English |
|---|---|
| Pages (from-to) | 57-64 |
| Number of pages | 8 |
| Journal | Chemistry and Physics of Lipids |
| Volume | 65 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 1993 Jan 1 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Biophysics
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Improved synthesis of (5Z)-7-(3-endo-{(benzenesulfonamido)-bicyclo[2.2.1]heptyl}hept-5-enoic acid (S-145) derivatives and their iodine-125-labeled radioligands for the study of thromboxane A2 receptor. / Kan, Wai-Ming; Tai, Hsin Hsiung.
In: Chemistry and Physics of Lipids, Vol. 65, No. 1, 01.01.1993, p. 57-64.Research output: Contribution to journal › Article
TY - JOUR
T1 - Improved synthesis of (5Z)-7-(3-endo-{(benzenesulfonamido)-bicyclo[2.2.1]heptyl}hept-5-enoic acid (S-145) derivatives and their iodine-125-labeled radioligands for the study of thromboxane A2 receptor
AU - Kan, Wai-Ming
AU - Tai, Hsin Hsiung
PY - 1993/1/1
Y1 - 1993/1/1
N2 - An improved synthetic scheme for (5Z)-7-{3-endo-[(benzenesulfonamido)-bicyclo[2.2.1]heptyl}-hept-5-enoic acid (S145) and its analogs has been designed. The procedure involves direct sulfonylation of 2-allyl-3-aminobicyclo[2.2.1]heptane intermediate followed by ozonolysis and addition of a C5 carboxyl unit. The yield of the final product was significantly improved. (5Z)-7-{3-endo-[(4-iodobenzensulfonamido)-bicyclo [2.2.1]heptyl}hept-5-enoic acid (HS-145) and (5Z)-7-{3-endo-[(4-hydroxy-benzensulfonamido)-bicyclo [2.2.1]heptyl}hept-5-enoic acid (HS-145) were synthesized directly without any protection and deprotection steps. [125I](5Z)-7-{3-endo-[(4-iodobenzensulfonamido)- bicyclo[2.2.1]heptyl}hept-5-enoic acid ([125I]HS-145) was prepared from IS-145 through an organotin intermediate and [125I]sodium iodide with high specific radioactivity and good recovery of radioactivity. [125I](5Z)-7-{3-endo-[(4-hydroxy 3-iodo-benzensulfonamido)-bicyclo[2.2.1]-heptyl}hept-5-enoic acid ([125I]HS-145) was prepared by direct iodination with sodium iodide using a modified chloramine-T method. Both [125]HS-145 and [125I]HS-145 were found to be valuable radioligands for studying thromboxane A2 (TXA2) receptor.
AB - An improved synthetic scheme for (5Z)-7-{3-endo-[(benzenesulfonamido)-bicyclo[2.2.1]heptyl}-hept-5-enoic acid (S145) and its analogs has been designed. The procedure involves direct sulfonylation of 2-allyl-3-aminobicyclo[2.2.1]heptane intermediate followed by ozonolysis and addition of a C5 carboxyl unit. The yield of the final product was significantly improved. (5Z)-7-{3-endo-[(4-iodobenzensulfonamido)-bicyclo [2.2.1]heptyl}hept-5-enoic acid (HS-145) and (5Z)-7-{3-endo-[(4-hydroxy-benzensulfonamido)-bicyclo [2.2.1]heptyl}hept-5-enoic acid (HS-145) were synthesized directly without any protection and deprotection steps. [125I](5Z)-7-{3-endo-[(4-iodobenzensulfonamido)- bicyclo[2.2.1]heptyl}hept-5-enoic acid ([125I]HS-145) was prepared from IS-145 through an organotin intermediate and [125I]sodium iodide with high specific radioactivity and good recovery of radioactivity. [125I](5Z)-7-{3-endo-[(4-hydroxy 3-iodo-benzensulfonamido)-bicyclo[2.2.1]-heptyl}hept-5-enoic acid ([125I]HS-145) was prepared by direct iodination with sodium iodide using a modified chloramine-T method. Both [125]HS-145 and [125I]HS-145 were found to be valuable radioligands for studying thromboxane A2 (TXA2) receptor.
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U2 - 10.1016/0009-3084(93)90081-D
DO - 10.1016/0009-3084(93)90081-D
M3 - Article
VL - 65
SP - 57
EP - 64
JO - Chemistry and Physics of Lipids
JF - Chemistry and Physics of Lipids
SN - 0009-3084
IS - 1
ER -