1018-71-9

• 常用中文名：硝吡咯菌素
• 常用英文名：Pyrrolnitrin
• CAS号：1018-71-9
• 分子式：C₁₀H₆Cl₂N₂O₂
• 分子量：257.07300
• 相关类别： 信号通路 抗感染 细菌
• 发布时间：2018-04-23 08:00:00
• 更新时间：2024-01-07 17:55:27
• Pyrrolnitrin 是从吡咯假单胞菌中分离出来的一种抗生素 (antibiotic)。Pyrrolnitrin 对真菌、酵母和革兰氏阳性菌具有广泛的抗菌活性。

名称

• 中文名: 硝吡咯菌素
• 英文名: pyrrolnitrin
• 中文别名: 吡咯尼林
• 英文别名: Pyrrolnitrine; Pyrrolnitrin; Pirrolnitrina; Pyroace; 3-chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole; Pyrrolnitrinum

物化性质

• 密度: 1.523g/cm3
• 沸点: 410.5ºC at 760mmHg
• 分子式: C₁₀H₆Cl₂N₂O₂
• 分子量: 257.07300
• 闪点: 202.1ºC
• 精确质量: 255.98100
• PSA: 61.61000
• LogP: 4.41990
• 蒸汽压: 1.42E-06mmHg at 25°C
• 折射率: 1.65
• 储存条件: 库房低温通风干燥
• 计算化学:

  1.疏水参数计算参考值（XlogP）:无

  2.氢键供体数量:1

  3.氢键受体数量:2

  4.可旋转化学键数量:1

  5.互变异构体数量:无

  6.拓扑分子极性表面积:61.6

  7.重原子数量:16

  8.表面电荷:0

  9.复杂度:272

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

生物活性

• 描述: Pyrrolnitrin 是从吡咯假单胞菌中分离出来的一种抗生素 (antibiotic)。Pyrrolnitrin 对真菌、酵母和革兰氏阳性菌具有广泛的抗菌活性。
• 相关类别:
  研究领域 >> 感染
  信号通路 >> 抗感染 >> 真菌
  信号通路 >> 抗感染 >> 细菌
• 靶点:

  Target: fungi, yeast and gram-positive bacteria[1]

• 体外研究: 吡咯烷腈(0-100μg/ml)对不同MIC值的细菌和真菌具有抗菌活性。对金黄色葡萄球菌、分枝杆菌、枯草芽孢杆菌、白色念珠菌、黑曲霉、红色毛癣菌的MIC值分别为50μg/ml、100μg/ml、0.78μg/ml、10μg/ml、12.5μg/ml和1μg/ml[1]。吡咯烷腈(0-100μg/ml)在微量滴定板法中具有抗菌作用。它对氧化节杆菌ATCC 14358、凝固酶芽孢杆菌ATCC 7050、地衣芽孢杆菌ATCC 14580、枯草芽孢杆菌ATCC 6051和苏云金杆菌ATCC 10792的MIC为6.25μg/ml[2]。
• 参考文献:

  [1]. K H van Pée, et al. Biosynthesis of Pyrrolnitrin and Other Phenylpyrrole Derivatives by Bacteria. Nat Prod Rep. 2000 Apr;17(2):157-64.

  [2]. N el-Banna, et al. Pyrrolnitrin From Burkholderia Cepacia: Antibiotic Activity Against Fungi and Novel Activities Against Streptomycetes.J Appl Microbiol. 1998 Jul;85(1):69-78.

  [3]. R S Gordee, et al.Systemic Antifungal Activity of Pyrrolnitrin.Appl Microbiol. 1969 May;17(5):690-4.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : UX9450000 CHEMICAL NAME : Pyrrole, 3-chloro-4-(3-chloro-2-nitrophenyl)- CAS REGISTRY NUMBER : 1018-71-9 BEILSTEIN REFERENCE NO. : 1287646 LAST UPDATED : 199612 DATA ITEMS CITED : 7 MOLECULAR FORMULA : C10-H6-Cl2-N2-O2 MOLECULAR WEIGHT : 257.08 WISWESSER LINE NOTATION : T5MJ CG DR CG BNW 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 : >2 gm/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Gastrointestinal - relaxation (isolated tissue) REFERENCE : JAJAAA Journal of Antibiotics, Series A. (Tokyo, Japan) V.6-20, 1953-67. For publisher information, see JANTAJ. Volume(issue)/page/year: 18,211,1965 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 68 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Gastrointestinal - relaxation (isolated tissue) REFERENCE : JAJAAA Journal of Antibiotics, Series A. (Tokyo, Japan) V.6-20, 1953-67. For publisher information, see JANTAJ. Volume(issue)/page/year: 18,211,1965 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >2400 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JAJAAA Journal of Antibiotics, Series A. (Tokyo, Japan) V.6-20, 1953-67. For publisher information, see JANTAJ. Volume(issue)/page/year: 18,211,1965 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1 gm/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Gastrointestinal - relaxation (isolated tissue) REFERENCE : JAJAAA Journal of Antibiotics, Series A. (Tokyo, Japan) V.6-20, 1953-67. For publisher information, see JANTAJ. Volume(issue)/page/year: 18,211,1965 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 86 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Gastrointestinal - relaxation (isolated tissue) REFERENCE : JAJAAA Journal of Antibiotics, Series A. (Tokyo, Japan) V.6-20, 1953-67. For publisher information, see JANTAJ. Volume(issue)/page/year: 18,211,1965 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 2 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 5,44,1981 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 105 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Gastrointestinal - relaxation (isolated tissue) REFERENCE : JAJAAA Journal of Antibiotics, Series A. (Tokyo, Japan) V.6-20, 1953-67. For publisher information, see JANTAJ. Volume(issue)/page/year: 18,211,1965

安全

• 海关编码: 2933990090

合成路线

1126425-93-1 ~71% 1018-71-9

文献：Morrison, Matthew D.; Hanthorn, Jason J.; Pratt, Derek A. Organic Letters, 2009 , vol. 11, # 5 p. 1051 - 1054

16386-65-5 ~% 1018-71-9

文献：Angewandte Chemie, , vol. 106, # 3 p. 346 - 347

153-97-9 ~% 1018-71-9

文献：Angewandte Chemie, , vol. 92, # 10 p. 855 - 856

海关

海关编码	2933990090
中文概述	2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%
申报要素	品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%