SU188971A1 - ATAIPPO-4 " - Google Patents
ATAIPPO-4 "Info
- Publication number
- SU188971A1 SU188971A1 SU1040513A SU1040513A SU188971A1 SU 188971 A1 SU188971 A1 SU 188971A1 SU 1040513 A SU1040513 A SU 1040513A SU 1040513 A SU1040513 A SU 1040513A SU 188971 A1 SU188971 A1 SU 188971A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mol
- calculated
- solvent
- acid
- found
- Prior art date
Links
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 230000000855 fungicidal Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- UTZPGFZOSLGODE-UHFFFAOYSA-N oxo(phenyl)-$l^{5}-arsane Chemical compound O=[AsH2]C1=CC=CC=C1 UTZPGFZOSLGODE-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Description
СПОСОБ ПОЛУЧЕНИЯ р-АЦИЛОКСИЭТИЛТИОАРСЕНИТОВMETHOD OF OBTAINING p-ACYLOXYETHYLTIOARSENITES
Пзобретение относитс к области получени новых мышь корганических соединений.The invention relates to the field of obtaining new mice with organic compounds.
Предложен снособ получени р-ацилоксиэтилтиоарсенитов общей формулыA procedure for the production of p-acyloxyethylthioarsenite of the general formula is provided.
КпАз(5С2П40Ас)з- , где п О-2, R- алкил, арил, Ас-анион органической кислоты. Снособ заключаетс в том, что соответствующие ангидриды или хлорангидриды мыщь ковистых кислот подвергают взаимодействию с р-меркаптоэтиловыми эфирами карбоновых кислот. Процесс провод т при кип чении смеси реагентов в среде органического растворител , например толуола. Вместо р-меркаптоэтиловых эфиров карбоновых кислот можно использовать полупродукты их синтеза.КпАз (5С2П40Ас) з-, where п О-2, R-alkyl, aryl, Ac-anion of an organic acid. The method consists in that the corresponding anhydrides or acid chlorides of the covoid acids are reacted with the carboxylic acid p-mercaptoethyl esters. The process is carried out by boiling the mixture of reagents in an organic solvent, for example toluene. Instead of the p-mercaptoethyl esters of carboxylic acids, it is possible to use intermediates for their synthesis.
Полученные соединени могут быть использованы в качестве фунгицидов.The compounds obtained can be used as fungicides.
Пример 1. Получение дибутил-5-(р-ацетилоксиэтилтио )-арсенита.Example 1. Getting dibutyl-5- (p-acetyloxyethylthio) -arsenite.
Смесь 0,02 г-моль дибутиларсинхлорида и 0,02 г-моль р-меркаптоэтилацетата в 20 мл толуола кип т т с обратным холодильником в атмосфере азота до прекращени выделени хлористого водорода (4-5 час). Растворитель отгон ют в вакууме, в остатке получают продукт, дл которого По 1,5049; df 1,1291; MRo: найдено 80,8; вычислено 80,7.A mixture of 0.02 gmol dibutylsarsinchloride and 0.02 gm mol p-mercapto ethyl acetate in 20 ml of toluene is refluxed under nitrogen until the evolution of hydrogen chloride stops (4-5 hours). The solvent is distilled off in vacuo, the residue gives the product, for which, 1.5049; df 1,1291; MRo: found 80.8; calculated 80.7.
Вычислено в о/о: As 24,35.Calculated in o / o: As 24.35.
Пример 2. Получение фенил-бис-5,5-(рацетилоксиэтилдитио )-арсенита.Example 2. Preparation of phenyl bis-5, 5- (racetyloxyethyldithio) -arsenite.
Смесь 0,02 г-моль фениларсиноксида и 0,02 г-моль р-меркаптоэтилацетата в 30 мл бензола кип т т в приборе Дина-Старка до прекращени выделени воды (2-3 час). Растворитель отгон ют в вакууме, в остатке получают продукт, дл которого: OD 1,5900; bf 1,3744; MRo: найдено 95,8; вычислено 94,9.A mixture of 0.02 gm-mol of phenylarsin oxide and 0.02 g-mol of p-mercapto ethyl acetate in 30 ml of benzene is boiled in a Dean-Stark apparatus until the evolution of water stops (2-3 hours). The solvent is distilled off in vacuo, the residue is the product, for which: OD 1.5900; bf 1.3744; MRo: found 95.8; calculated 94.9.
Найдено в о/ц: As 19,00.Found in o / c: As 19.00.
CuHigAsOiSs.CuHigAsOiSs.
Вычислено в о/о: Аз 19,23.Calculated in o / o: Az 19.23.
Пример 3. Получение дифенил р-феноксиацетоксиэтилтиоарсенита .Example 3. Getting diphenyl p-phenoxyacetoxyethylthioarsenite.
0,02 г-моль ангидрида дифениларсинистой кислоты и 0,04 г-моль феноксиуксусной кислоты в 30 мл толуола по капл м добавл ют 0,04 г-моль р-меркантоэтанола и кип т т в приборе Дина-Старка до прекращени выделени воды (5-6 час). Растворитель отгон ют в вакууме, в остатке получают продукт, дл которого 1,6260; df 1,3271; MRo: найдено 117,2; вычислено 116,5.0.04 g mol of diphenylarcinic acid anhydride and 0.04 g mol of phenoxyacetic acid in 30 ml of toluene were added dropwise 0.04 g mol of p-mercantoethanol and boiled in a Dean-Stark apparatus until the evolution of water ceased ( 5-6 hours). The solvent is distilled off in vacuo, the residue gives the product for which 1.6260; df 1.3271; MRo: found 117.2; calculated 116.5.
В описанных услови х получают другие вещества , свойства которых и данные анализа приведены в таблице.Under the conditions described, other substances are obtained, the properties of which and the analysis data are listed in the table.
Предмет изобретени Subject invention
Способ получени р-ацнлоксиэтилтиоарсеннтов общей формулы R,,As(SC2H4OAc)The method of obtaining p-atsnloxyethylthioarsents of the general formula R ,, As (SC2H4OAc)
где п 0-2, R-алкил или арил, Ас-аннон органической кислоты, отличающийс тем, что ангидриды или хлорангидриды мышь ковистых кислот подвергают взаимодействию с р-меркаптоэтиловыми эфирами карбоновых кислот или полупродуктами их синтеза при кип чении смесн реагентов в среде органического ,растворител , например толуола.where p 0-2, R-alkyl or aryl, Ac-annon of an organic acid, characterized in that mouse anhydrides or acid chlorides of covoid acids react with p-mercaptoethyl esters of carboxylic acids or intermediates for their synthesis while boiling the reagent mix in organic medium, solvent, for example toluene.
ТаблицаTable
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU188971A1 true SU188971A1 (en) |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006020048A2 (en) * | 2004-07-16 | 2006-02-23 | The Texas A & M University System | Compounds and methods for treatment of cancer |
| US7619000B2 (en) | 2002-01-07 | 2009-11-17 | The Texas A&M University System | S-dimethylarsino-thiosuccinic acid S-dimethylarsino-2-thiobenzoic acid S-(dimethylarsino) glutathione as treatments for cancer |
| US8252773B2 (en) | 2007-11-02 | 2012-08-28 | Ziopharm Oncology, Inc. | Combination therapy with organic arsenicals |
| US8334398B2 (en) | 2005-07-29 | 2012-12-18 | Ziopharm Oncology, Inc. | Compounds and methods for the treatment of cancer |
| US8796329B2 (en) | 2006-09-29 | 2014-08-05 | Ziopharm Oncology, Inc. | Method for controlling angiogenesis in animals |
| US10842769B2 (en) | 2008-08-20 | 2020-11-24 | Solasia Pharma K.K. | Organoarsenic compounds and methods for the treatment of cancer |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7619000B2 (en) | 2002-01-07 | 2009-11-17 | The Texas A&M University System | S-dimethylarsino-thiosuccinic acid S-dimethylarsino-2-thiobenzoic acid S-(dimethylarsino) glutathione as treatments for cancer |
| WO2006020048A2 (en) * | 2004-07-16 | 2006-02-23 | The Texas A & M University System | Compounds and methods for treatment of cancer |
| US7405314B2 (en) | 2004-07-16 | 2008-07-29 | The Texas A&M University System | Compounds and methods for the treatment of cancer |
| US8334398B2 (en) | 2005-07-29 | 2012-12-18 | Ziopharm Oncology, Inc. | Compounds and methods for the treatment of cancer |
| US8865764B2 (en) | 2005-07-29 | 2014-10-21 | Solasia Pharma K.K. | Compounds and methods for the treatment of cancer |
| US8796329B2 (en) | 2006-09-29 | 2014-08-05 | Ziopharm Oncology, Inc. | Method for controlling angiogenesis in animals |
| US8252773B2 (en) | 2007-11-02 | 2012-08-28 | Ziopharm Oncology, Inc. | Combination therapy with organic arsenicals |
| US10842769B2 (en) | 2008-08-20 | 2020-11-24 | Solasia Pharma K.K. | Organoarsenic compounds and methods for the treatment of cancer |
| US11324714B2 (en) | 2008-08-20 | 2022-05-10 | Solasia Pharma K.K. | Organoarsenic compounds and methods for the treatment of cancer |
| US11324713B2 (en) | 2008-08-20 | 2022-05-10 | Solasia Pharma K.K. | Organoarsenic compounds and methods for the treatment of cancer |
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