JPS584797A - ５′−Ｓｅ−（２−ニトロフエニル）セレノヌクレオシドとその合成法 - Google Patents
５′−Ｓｅ−（２−ニトロフエニル）セレノヌクレオシドとその合成法Info
- Publication number
- JPS584797A JPS584797A JP9970881A JP9970881A JPS584797A JP S584797 A JPS584797 A JP S584797A JP 9970881 A JP9970881 A JP 9970881A JP 9970881 A JP9970881 A JP 9970881A JP S584797 A JPS584797 A JP S584797A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- nitrophenyl
- nucleus
- substituent
- selenonucleoside
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title description 2
- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
- 239000002777 nucleoside Substances 0.000 claims abstract description 8
- 150000003833 nucleoside derivatives Chemical class 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 7
- 150000003230 pyrimidines Chemical class 0.000 claims abstract description 7
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims abstract description 5
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 4
- LHBLJWULWKQRON-UHFFFAOYSA-N (2-nitrophenyl) selenocyanate Chemical compound [O-][N+](=O)C1=CC=CC=C1[Se]C#N LHBLJWULWKQRON-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 14
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 7
- 150000003838 adenosines Chemical class 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 2
- 241000223104 Trypanosoma Species 0.000 abstract 1
- DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000003835 nucleoside group Chemical group 0.000 description 3
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 229960005305 adenosine Drugs 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9970881A JPS584797A (ja) | 1981-06-29 | 1981-06-29 | ５′−Ｓｅ−（２−ニトロフエニル）セレノヌクレオシドとその合成法 |
| US06/393,254 US4552955A (en) | 1981-06-29 | 1982-06-29 | Process for the synthesis of 4',5'-unsaturated nucleosides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9970881A JPS584797A (ja) | 1981-06-29 | 1981-06-29 | ５′−Ｓｅ−（２−ニトロフエニル）セレノヌクレオシドとその合成法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS584797A true JPS584797A (ja) | 1983-01-11 |
| JPS6365076B2 JPS6365076B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-12-14 |
Family
ID=14254562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9970881A Granted JPS584797A (ja) | 1981-06-29 | 1981-06-29 | ５′−Ｓｅ−（２−ニトロフエニル）セレノヌクレオシドとその合成法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS584797A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
-
1981
- 1981-06-29 JP JP9970881A patent/JPS584797A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6365076B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-12-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4980460A (en) | Protected nucleosides which permit more efficient oligonucleotide syntheses | |
| AU711814B2 (en) | Nucleoside derivatives with photolabile protective groups | |
| CN110719912B (zh) | 在可见光区能进行光交联的光响应性核苷酸类似物 | |
| Yao-Zhong et al. | Synthesis and duplex stability of oligodeoxynucleotides containing 6-mercaptopurine | |
| Whistler et al. | 4-Thio-D-arabinofuranosylpyrimidine nucleosides | |
| CN110914278B (zh) | 在可见光区能进行光交联的光响应性核苷酸类似物 | |
| Napoli et al. | Synthesis of [1-15N]-labeled 2'-deoxyinosine and 2'-deoxyadenosine | |
| Kazimierczuk et al. | Methylation of adenosine in strongly alkaline medium: Preparation and Properties of o'-methyl derivatives of adenosine and N6-methyladenosine | |
| US5204456A (en) | Derivatives of nucleosides and their use for the synthesis of oligonucleotides | |
| JPS584797A (ja) | ５′−Ｓｅ−（２−ニトロフエニル）セレノヌクレオシドとその合成法 | |
| JP2003513101A (ja) | 感光性保護基を有するヌクレオシド誘導体 | |
| Beylin et al. | Anticancer anthrapyrazoles. Improved syntheses of clinical agents CI‐937, CI‐941, and piroxantrone hydrochloride | |
| Zlatev et al. | Convenient synthesis of N2-isobutyryl-2′-O-methyl guanosine by efficient alkylation of O6-trimethylsilylethyl-3′, 5′-di-tert-butylsilanediyl guanosine | |
| US4552955A (en) | Process for the synthesis of 4',5'-unsaturated nucleosides | |
| JPS584780A (ja) | ４′，５′−不飽和ヌクレオシドの合成法 | |
| JP2009519325A (ja) | ２’、２’−ジフルオロヌクレオシドと中間体の製造プロセス | |
| WO2000039144A1 (fr) | Procede de preparation de derives fluores de nucleosides et de sucres | |
| JPH013194A (ja) | ２′−ブロモ−２′，３′−ジデヒドロ−２′，３′−ジデオキシシチジン及びその製造法 | |
| KR930008632B1 (ko) | 우라실 유도체를 시토신 유도체로 전환시키는 방법 | |
| JPH02160799A (ja) | ２′−デオキシ−β−アデノシンの製造法 | |
| JPH03264582A (ja) | ２’，３’―ジデオキシ―２’，３’―ジ置換―ヌクレオシド類とその製造方法 | |
| GB2096596A (en) | 8-quinolinesulfonyl derivatives and their synthesis and use as coupling agents in nucleotide chemistry | |
| JPH0296589A (ja) | ヌクレオシド類 | |
| JP2021020883A (ja) | 光応答性ヌクレオチドアナログ | |
| Zhang et al. | A convenient synthesis of N-linked diglycose derivatives based on one-pot tandem Staudinger/aza-Wittig/reduction and biological evaluation |