1874-54-0

• 常用中文名：Psicofuranine
• 常用英文名：Psicofuranine
• CAS号：1874-54-0
• 分子式：C₁₁H₁₅N₅O₅
• 分子量：297.26700
• 相关类别： 信号通路 抗感染 细菌
• 发布时间：2016-09-05 20:33:29
• 更新时间：2024-01-07 22:14:39
• Psicofuramine 是一种核苷抗生素,具有抑制黄嘌呤 5'-磷酸氨化酶的作用。Psicofuramine 还可以特异性抑制 GMP 合酶,并中断寄生虫的生长。Psicofuramine 对恶性疟原虫的生长具有剂量依赖性抑制作用。

名称

• 中文名: 二十烷呋喃酮
• 英文名: (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-2,5-bis(hydroxymethyl)oxolane-3,4-diol
• 英文别名: Adenine,9beta-D-psicofuranosyl; 6-Amino-9-D-psicofuranosylpurine; Psicofuranosyladenine; Angustmycin C; psicofuranine; angustmicine C

物化性质

• 密度: 2.02g/cm3
• 沸点: 720.1ºC at 760 mmHg
• 分子式: C₁₁H₁₅N₅O₅
• 分子量: 297.26700
• 闪点: 389.3ºC
• 精确质量: 297.10700
• PSA: 159.77000
• 蒸汽压: 9.24E-22mmHg at 25°C
• 折射率: 1.855
• 储存条件: -20°C，密闭，干燥

生物活性

• 描述: Psicofuramine 是一种核苷抗生素,具有抑制黄嘌呤 5'-磷酸氨化酶的作用。Psicofuramine 还可以特异性抑制 GMP 合酶,并中断寄生虫的生长。Psicofuramine 对恶性疟原虫的生长具有剂量依赖性抑制作用。
• 相关类别:
  研究领域 >> 感染
  信号通路 >> 抗感染 >> 细菌
• 靶点:

  Xanthosine 5'-phosphate aminase[2] P. falciparum[1] E. coli[1]

• 体外研究: Psicofuranine特异性地抑制细菌GMP合酶,通过分离编码GMP合酶基因突变的抗Psicofuranine大肠杆菌突变体和抑制细菌生长证明了这一点。Psicofuranine对恶性疟原虫生长具有剂量依赖性抑制作用,IC50为0.3mm。Psicofuranine的抑制浓度与大肠杆菌相似[1]。
• 参考文献:

  [1]. cConkey GA. Plasmodium falciparum: isolation and characterisation of a gene encoding protozoan GMP synthase. Exp Parasitol. 2000 Jan;94(1):23-32.

  [2]. UDAKA S, et al. INHIBITION OF PARENTAL AND MUTANT XANTHOSINE 5'-PHOSPHATE AMINASES BY PSICOFURANINE. J Biol Chem. 1963 Aug;238:2797-803.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : AU7100000 CHEMICAL NAME : Adenine, 9-beta-D-psicofuranosyl- CAS REGISTRY NUMBER : 1874-54-0 BEILSTEIN REFERENCE NO. : 0095142 LAST UPDATED : 199612 DATA ITEMS CITED : 7 MOLECULAR FORMULA : C11-H15-N5-O5 MOLECULAR WEIGHT : 297.31 WISWESSER LINE NOTATION : T56 BN DN FN HNJ IZ D- BT5OTJ B1Q CQ DQ E1Q 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 : 10 gm/kg TOXIC EFFECTS : Tumorigenic - active as anti-cancer agent REFERENCE : ANTCAO Antibiotics and Chemotherapy (Washington, DC). (Washington, DC) V.1-12, 1951-62. For publisher information, see CLMEA3. Volume(issue)/page/year: 9,675,1959 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 13 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,842,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1695 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : UPJOH* "Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." (Kalamazoo, MI 49001) Volume(issue)/page/year: 2(6),-,1971 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 6 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,842,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : >10 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : UPJOH* "Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." (Kalamazoo, MI 49001) Volume(issue)/page/year: 2(6),-,1971 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 9800 mg/kg/28D-I TOXIC EFFECTS : Liver - other changes Blood - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain REFERENCE : ANTCAO Antibiotics and Chemotherapy (Washington, DC). (Washington, DC) V.1-12, 1951-62. For publisher information, see CLMEA3. Volume(issue)/page/year: 9,675,1959 *** REVIEWS *** TOXICOLOGY REVIEW CRTXB2 CRC Critical Reviews in Toxicology. (CRC Press, Inc., 2000 Corporate Blvd., NW, Boca Raton, FL 33431) V.1- 1971- Volume(issue)/page/year: 2,159,1973

合成路线

138348-93-3 ~90% 1874-54-0

文献：Mahmood; Vasella; Bernet Helvetica Chimica Acta, 1991 , vol. 74, # 7 p. 1555 - 1584

93417-25-5 ~50% 1874-54-0

文献：Grouiller; Chattopadhyaya 1984 , vol. 38, # 5 B p. 367 - 373

138348-91-1 ~74% 1874-54-0

文献：Mahmood; Vasella; Bernet Helvetica Chimica Acta, 1991 , vol. 74, # 7 p. 1555 - 1584

138348-88-6 ~% 1874-54-0

文献：Mahmood; Vasella; Bernet Helvetica Chimica Acta, 1991 , vol. 74, # 7 p. 1555 - 1584

18055-47-5 ~% 1874-54-0

文献：Mahmood; Vasella; Bernet Helvetica Chimica Acta, 1991 , vol. 74, # 7 p. 1555 - 1584

87-42-3 ~% 1874-54-0

文献：Grouiller; Chattopadhyaya 1984 , vol. 38, # 5 B p. 367 - 373

13019-85-7 ~% 1874-54-0

文献：Grouiller; Chattopadhyaya 1984 , vol. 38, # 5 B p. 367 - 373

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