螺佐呋酮
螺佐呋酮用途
用于胃溃疡。
螺佐呋酮名称
[ CAS 号 ]:
72492-12-7
[ 中文名 ]:
螺佐呋酮
[ 英文名 ]:
SPIZOFURONE
[中文别名 ]:
[英文别名 ]:
- Maon
- AG-629
- Espizofurona [spanish]
- Spizofuronum
- Espizofurona
- 1'-cyclopropane]-3-one
- 5-acetylspiro[benzo[b]furan-2(3H)
螺佐呋酮物理化学性质
[ 密度 ]:
1.33 g/cm3
[ 沸点 ]:
396.3ºC at 760 mmHg
[ 熔点 ]:
150-155ºC
[ 分子式 ]:
C12H10O3
[ 分子量 ]:
202.20600
[ 闪点 ]:
180.6ºC
[ 精确质量 ]:
202.06300
[ PSA ]:
43.37000
[ LogP ]:
1.99690
[ 折射率 ]:
1.61
螺佐呋酮毒性和生态
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- WG9807500
- CHEMICAL NAME :
- Spiro(benzofuran-2(3H),1'-cyclopropan)-3-one, 5-acetyl-
- CAS REGISTRY NUMBER :
- 72492-12-7
- LAST UPDATED :
- 199612
- DATA ITEMS CITED :
- 9
- MOLECULAR FORMULA :
- C12-H10-O3
- MOLECULAR WEIGHT :
- 202.22
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 5440 mg/kg
- TOXIC EFFECTS :
- Behavioral - altered sleep time (including change in righting reflex) Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease
- REFERENCE :
- KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,541,1986
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 609 mg/kg
- TOXIC EFFECTS :
- Behavioral - altered sleep time (including change in righting reflex) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
- REFERENCE :
- KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,541,1986
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 1610 mg/kg
- TOXIC EFFECTS :
- Behavioral - altered sleep time (including change in righting reflex) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
- REFERENCE :
- KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,541,1986
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1740 mg/kg
- TOXIC EFFECTS :
- Behavioral - altered sleep time (including change in righting reflex) Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease
- REFERENCE :
- KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,541,1986
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 840 mg/kg
- TOXIC EFFECTS :
- Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Nutritional and Gross Metabolic - body temperature decrease
- REFERENCE :
- KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,541,1986
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1770 mg/kg
- TOXIC EFFECTS :
- Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
- REFERENCE :
- KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,541,1986 ** OTHER MULTIPLE DOSE TOXICITY DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 35 gm/kg/5W-C
- TOXIC EFFECTS :
- Gastrointestinal - other changes Liver - other changes
- REFERENCE :
- KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,547,1986
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 18200 mg/kg/26W-C
- TOXIC EFFECTS :
- Liver - other changes Related to Chronic Data - death
- REFERENCE :
- KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,577,1986
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 10500 mg/kg/5W-C
- TOXIC EFFECTS :
- Liver - other changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases
- REFERENCE :
- KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,559,1986
螺佐呋酮合成路线
螺佐呋酮上下游产品
螺佐呋酮上游产品
螺佐呋酮下游产品
螺佐呋酮制备
方法l：在室温和搅拌下，将5-乙酰基-2-羟基苯甲酸甲酯(8.0mol)加到1.32kg碳酸钾在2.0L二甲基甲酰胺的悬浮中。在60℃加热1h后，在5℃和3h内加入1.32kgα-溴-γ-丁内酯。加毕在45℃下搅拌10h。冷却，过滤除去不溶的无机物。滤液减压浓缩，剩余物真空蒸馏以移去没有反应的5-乙酰基-2-羟基苯甲酸甲酯。剩余物(粗品化合物(I)，用甲醇重结晶后，熔点112～113℃)溶于2L甲醇和2L 50%氢氧化钠水溶液。并于60℃加热。冷却后，将反应液倾入1.5L冰水，用2.2L浓盐酸酸化。过滤收集析出的沉淀，水洗，干燥。溶于1L二氧六烷和1L甲苯。加入400g对甲苯磺酸，在装有分水器的装置中加热回流8.5h。减压浓缩，剩余物倾入10L冰水。过滤收集析出的沉淀，水洗，干燥，溶于乙酸乙酯。干燥后浓缩，用丙酮-甲醇重结晶，得化合物(Ⅱ)，总收率45%，熔点155～158℃。
1.26mol化合物(Ⅱ)在2.8L乙酸酐的溶液和560ml三乙胺加热回流。减压浓缩，剩余物倾人3L冰水。过滤收集析出的沉淀，洗涤后，用甲醇重结晶，得化合物(Ⅲ)，收率55%，熔点132～134℃。
7.4mol化合物(Ⅲ)和94g氯化钠溶于1.5L二甲亚砜，在150℃下搅拌1.5h。冷却后，倾入冰水。过滤收集析出的沉淀，水洗，干燥，用乙醇重结晶，得螺佐呋酮，收率88%，熔点。102～104℃。
从化合物(I)也可直接得到化合物(Ⅲ)。化合物(I)(4.7mmol)在15ml乙酸酐的溶液和3ml三乙胺加热回流10h。减压浓缩，剩余物倾入冰水，用乙酸乙酯提取。提取液水洗，干燥，减压浓缩。剩余物用硅胶层析，四氯化碳-丙酮(5：1，体积比)洗脱。收集第二组分洗脱液，用甲醇重结晶，得化合物(Ⅲ)，收率47%。
方法2：一步合成法。以5-乙酰基-2-[(四氢-2-氧-3-呋喃基)氧]苯甲酸甲酯(化合物(I))为原料，可一步反应得到螺佐呋酮，但对试剂要求较高。
将4.17g1，5-二氮双环[5．4．0]十一烯-5(DBU)和67g氯化钠溶于1L二甲基甲酰胺，在150℃和搅拌下，于2h内滴加5-乙酰基-2-[(四氢-2-氧-3-呋喃基)氧]苯甲酸甲酯(278g，lmo1)在1.8L二甲基甲酰胺的溶液，加毕再搅拌2h。减压蒸去溶剂，剩余物用水稀释后，用二氯甲烷提取。提取液洗涤，干燥，通过硅胶进行脱色。二氯甲烷溶液减压浓缩，产生的结晶再用乙醇重结晶，得136g螺佐呋酮，收率67%，熔点106-107℃。
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