CAS: 87-11-6; N-(4-Methyl-5-Oxodithiolo[4,3-B]Pyrrol-6-yl)Acetamide

该化合物是化学化合物,其作用是生物和生化试剂,被归类为硫酸衍生物,并被确认具有抑制某些酶的能力,特别是核酸生物合成酶的能力.Thiolutin展示出黄色晶状,在有机溶剂中可溶解,使其在各种实验室应用中有用.其结构包括一个硫醇组,有助于其再活性和生物活动.在研究中,硫酸盐被用于研究细胞过程,并显示出抗微生物和抗癌活动的潜力.然而,必须谨慎处理硫酸,因为它可能构成健康风险,包括皮肤和呼吸刺激.在实验室环境中与该化合物合作时,应当遵循适当的安全议定书.

英文名称N-(4-Methyl-5-Oxodithiolo[4,3-B]Pyrrol-6-yl)Acetamide
中文名称硫藤黄素
IUPAC名称N-(4-methyl-5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide
其它别名1,2-Dithiolo[4,3-b]pyrrol-5(4H)-one,6-acetamido-4-methyl- (6CI,7CI); 1,2-Dithiolo[4,3-b]pyrrole, acetamide deriv.; 3-Acetamido-5-methylpyrrolin-4-one[4,3-d]-1,2-dithiole; Acetopyrrothin; N-(4,5-Dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)acetamide; Thiolutin
CAS编号87-11-6
MFCD编号:MFCD01076610
EINECS号:635-840-2
FDA UNII编号:02C005Q20B
分子式:C8H8N2O2S2分子量:228.29
产品CID: 2390278
产品分类原料药 → 抗生素类药物 → 其它抗生素类药

相似结构搜索
InChIKey: MHMRAFONCSQAIA-UHFFFAOYSA-N
InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)
计算化学: 氢键受体数4.0氢键供体数1.0可旋转键数1.0

物理性质

熔点273-276 °C
沸点478.6±45.0 °C at 760 mmHg
闪点243.3±28.7 °C
密度1.6±0.1 g/cm3
pKa:10.54±0.20(预测)
PSA:107.58
LogP:0.99
折射率1.721
蒸汽压0.0±1.2 mmHg at 25°C
溶解性DMSO: 5 mg/mL
外观形态1-丁醇中析出的亮黄色针状物黄色结晶性固体
储存条件−20°C
产品应用该化合物用于聚合酶II抑制剂:研究其对酵母细胞的影响,以计算转录半衰期,研究其在发芽酵母过程中发芽过程中对转录过程的影响,研究其对斑马鱼细胞粘合的影响

欧盟法规

ECHA物质C&L通报

上下游产品

合成工艺路线路线简述

142705-66-6 = 87-11-6
反应条件:1.1 Reagents: Bromine Solvents: Acetic Acid,Dichloromethane
标题:Condensed 1,2-Dithioles. I. Synthesis Of Thiolutine And Related Compounds
作者:Stachel,Hans Dietrich; Et Al
参考文献:Liebigs Annalen Der Chemie 日期:1992 卷标:(5) 页码:473-80]

608131-96-0 = 87-11-6
反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water
标题:Dithiolopyrrolones Are Prochelators That Are Activated By Glutathione
作者:Albini,Francesca; Et Al
参考文献:Chemistry - A European Journal 日期:2023 卷标:29(4)]

139101-88-5 = 87-11-6
反应条件:1.1 -2.1 Reagents: Lithium Iodide Solvents: Pyridine
标题:Condensed 1,2-Dithioles. I. Synthesis Of Thiolutine And Related Compounds
作者:Stachel,Hans Dietrich; Et Al
参考文献:Liebigs Annalen Der Chemie 日期:1992 卷标:(5) 页码:473-80]

928150-81-6 = 87-11-6
反应条件:1.1 Reagents: Sodium Hydride Solvents: Dimethylformamide2.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water
标题:Dithiolopyrrolones Are Prochelators That Are Activated By Glutathione
作者:Albini,Francesca; Et Al
参考文献:Chemistry - A European Journal 日期:2023 卷标:29(4)]

= 87-11-6
反应条件:1.1 Reagents: P-Toluenesulfonic Acid Solvents: Toluene2.1 Reagents: Nitric Acid3.1 Reagents: Sodium Dithionite Solvents: Acetic Anhydride4.1 Reagents: Lithium Iodide Solvents: Pyridine
标题:Condensed 1,2-Dithioles. I. Synthesis Of Thiolutine And Related Compounds
作者:Stachel,Hans Dietrich; Et Al
参考文献:Liebigs Annalen Der Chemie 日期:1992 卷标:(5) 页码:473-80]

4998-57-6 = 87-11-6 + 482656-54-2
反应条件:1.1 Reagents: Glucose,Calcium Carbonate,Sodium Hydroxide,Sulfuric Acid Magnesium Salt (1:1),Sodium Chloride,Dipotassium Phosphate,Monopotassium Phosphate,Ammonium Sulfate Solvents: Water; 72 H,Ph 7.0,30 °C
标题:Nutritional Requirements For The Production Of Dithiolopyrrolone Antibiotics By Saccharothrix Algeriensis Nrrl B-24137
作者:Bouras,Noureddine; Et Al
参考文献:Enzyme And Microbial Technology 日期:2006 卷标:39(7) 页码:1423-1429]

56-86-0 = 87-11-6 + 482656-54-2 + 482656-55-3 + 112843-01-3
反应条件:1.1 Reagents: Glucose,Calcium Carbonate,Sodium Hydroxide,Sulfuric Acid Magnesium Salt (1:1),Sodium Chloride,Dipotassium Phosphate,Monopotassium Phosphate,Ammonium Sulfate Solvents: Water; 72 H,Ph 7.0,30 °C
标题:Nutritional Requirements For The Production Of Dithiolopyrrolone Antibiotics By Saccharothrix Algeriensis Nrrl B-24137
作者:Bouras,Noureddine; Et Al
参考文献:Enzyme And Microbial Technology 日期:2006 卷标:39(7) 页码:1423-1429]

139102-08-2 = 87-11-6
反应条件:1.1 Reagents: Lithium Iodide Solvents: Pyridine
标题:Condensed 1,2-Dithioles. I. Synthesis Of Thiolutine And Related Compounds
作者:Stachel,Hans Dietrich; Et Al
参考文献:Liebigs Annalen Der Chemie 日期:1992 卷标:(5) 页码:473-80]

= 87-11-6
反应条件:1.1 Reagents: Potassium Bicarbonate Solvents: Ethanol,Methanol
标题:Total Synthesis Of The Antibiotics Thiolutin And Holomycin. Ii. Improved Introduction Of Mercapto Groups Into Pyrrolones
作者:Schmidt,Ulrich
参考文献:Chemische Berichte 日期:1964 卷标:97(5) 页码:1511-12]

56-89-3 = 87-11-6
反应条件:1.1 Reagents: Glucose,Calcium Carbonate,Sodium Hydroxide,Sulfuric Acid Magnesium Salt (1:1),Sodium Chloride,Dipotassium Phosphate,Monopotassium Phosphate,Ammonium Sulfate Solvents: Water; 72 H,Ph 7.0,30 °C
标题:Nutritional Requirements For The Production Of Dithiolopyrrolone Antibiotics By Saccharothrix Algeriensis Nrrl B-24137
作者:Bouras,Noureddine; Et Al
参考文献:Enzyme And Microbial Technology 日期:2006 卷标:39(7) 页码:1423-1429]

59-92-7 = 87-11-6
反应条件:1.1 Reagents: Glucose,Calcium Carbonate,Sodium Hydroxide,Sulfuric Acid Magnesium Salt (1:1),Sodium Chloride,Dipotassium Phosphate,Monopotassium Phosphate,Ammonium Sulfate Solvents: Water; 72 H,Ph 7.0,30 °C
标题:Nutritional Requirements For The Production Of Dithiolopyrrolone Antibiotics By Saccharothrix Algeriensis Nrrl B-24137
作者:Bouras,Noureddine; Et Al
参考文献:Enzyme And Microbial Technology 日期:2006 卷标:39(7) 页码:1423-1429]

139101-80-7 = 87-11-6
反应条件:1.1 -2.1 Reagents: Bromine Solvents: Acetic Acid,Dichloromethane
标题:Condensed 1,2-Dithioles. I. Synthesis Of Thiolutine And Related Compounds
作者:Stachel,Hans Dietrich; Et Al
参考文献:Liebigs Annalen Der Chemie 日期:1992 卷标:(5) 页码:473-80]

= 87-11-6
反应条件:1.1 Reagents: Sodium Dithionite Solvents: Acetic Anhydride2.1 Reagents: Lithium Iodide Solvents: Pyridine
标题:Condensed 1,2-Dithioles. I. Synthesis Of Thiolutine And Related Compounds
作者:Stachel,Hans Dietrich; Et Al
参考文献:Liebigs Annalen Der Chemie 日期:1992 卷标:(5) 页码:473-80]

139101-74-9 = 87-11-6
反应条件:1.1 Reagents: Nitric Acid2.1 Reagents: Sodium Dithionite Solvents: Acetic Anhydride3.1 Reagents: Lithium Iodide Solvents: Pyridine
标题:Condensed 1,2-Dithioles. I. Synthesis Of Thiolutine And Related Compounds
作者:Stachel,Hans Dietrich; Et Al
参考文献:Liebigs Annalen Der Chemie 日期:1992 卷标:(5) 页码:473-80]

139101-95-4 = 87-11-6
反应条件:1.1 Reagents: Bromine Solvents: Acetic Acid,Dichloromethane2.1 -3.1 Reagents: Lithium Iodide Solvents: Pyridine
标题:Condensed 1,2-Dithioles. I. Synthesis Of Thiolutine And Related Compounds
作者:Stachel,Hans Dietrich; Et Al
参考文献:Liebigs Annalen Der Chemie 日期:1992 卷标:(5) 页码:473-80]

63-91-2 = 87-11-6 + 482656-54-2 + 482656-55-3
反应条件:1.1 Reagents: Glucose,Calcium Carbonate,Sodium Hydroxide,Sulfuric Acid Magnesium Salt (1:1),Sodium Chloride,Dipotassium Phosphate,Monopotassium Phosphate,Ammonium Sulfate Solvents: Water; 72 H,Ph 7.0,30 °C
标题:Nutritional Requirements For The Production Of Dithiolopyrrolone Antibiotics By Saccharothrix Algeriensis Nrrl B-24137
作者:Bouras,Noureddine; Et Al
参考文献:Enzyme And Microbial Technology 日期:2006 卷标:39(7) 页码:1423-1429]

147-85-3 = 87-11-6 + 482656-54-2 + 482656-55-3 + 112843-01-3
反应条件:1.1 Reagents: Glucose,Calcium Carbonate,Sodium Hydroxide,Sulfuric Acid Magnesium Salt (1:1),Sodium Chloride,Dipotassium Phosphate,Monopotassium Phosphate,Ammonium Sulfate Solvents: Water; 72 H,Ph 7.0,30 °C
标题:Nutritional Requirements For The Production Of Dithiolopyrrolone Antibiotics By Saccharothrix Algeriensis Nrrl B-24137
作者:Bouras,Noureddine; Et Al
参考文献:Enzyme And Microbial Technology 日期:2006 卷标:39(7) 页码:1423-1429]

583-93-7 = 87-11-6 + 39859-18-2 + 482656-54-2 + 482656-55-3 + 112843-01-3
反应条件:1.1 Reagents: Glucose,Calcium Carbonate,Sodium Hydroxide,Sulfuric Acid Magnesium Salt (1:1),Sodium Chloride,Dipotassium Phosphate,Monopotassium Phosphate,Ammonium Sulfate Solvents: Water; 72 H,Ph 7.0,30 °C
标题:Nutritional Requirements For The Production Of Dithiolopyrrolone Antibiotics By Saccharothrix Algeriensis Nrrl B-24137
作者:Bouras,Noureddine; Et Al
参考文献:Enzyme And Microbial Technology 日期:2006 卷标:39(7) 页码:1423-1429]

657-27-2 = 87-11-6 + 39859-18-2 + 482656-54-2 + 482656-55-3 + 112843-01-3
反应条件:1.1 Reagents: Glucose,Calcium Carbonate,Sodium Hydroxide,Sulfuric Acid Magnesium Salt (1:1),Sodium Chloride,Dipotassium Phosphate,Monopotassium Phosphate,Ammonium Sulfate Solvents: Water; 72 H,Ph 7.0,30 °C
标题:Nutritional Requirements For The Production Of Dithiolopyrrolone Antibiotics By Saccharothrix Algeriensis Nrrl B-24137
作者:Bouras,Noureddine; Et Al
参考文献:Enzyme And Microbial Technology 日期:2006 卷标:39(7) 页码:1423-1429

📜5-Methyl-2,2-Diphenyl-1,3-Dithiino<5,4-B>Pyrrol-6(5H)-On置于三氯化铝,盐酸羟胺,溴,三氯氧磷体系中,用四氢呋喃,甲醇,二氯甲烷,溶剂黄146 作为反应溶剂,化学反应 38.0H,反应生成硫藤黄素
参考文献:Stachel,Hans-Dietrich; Nienaber,Juliane; Zoukas,Thomas,Liebigs Annalen Der Chemie,1992,# 5,P. 473-480
标题:Stachel,Hans-Dietrich; Nienaber,Juliane; Zoukas,Thomas,Liebigs Annalen Der Chemie,1992,# 5,P. 473-480

海关参考信息

2912110000-甲醛
2912120000-乙醛
2924199090-其他无环酰胺
2921199090-其他无环单胺
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-11851651-B2
优先权日:2017-06-19
标题 :Automated methods for scalable, parallelized enzymatic biopolymer synthesis and modification using microfluidic devices
发明人：BANAL JAMES; BERLEANT JOSEPH DON; SHEPHERD TYSON; BATHE MARK
权利人:MASSACHUSETTS INST TECHNOLOGY
摘要:Methods for the automated template-free synthesis of user-defined sequence controlled biopolymers using microfluidic devices are described. The methods facilitate simultaneous synthesis of up to thousands of uniquely addressed biopolymers from the controlled movement and combination of regents as fluid droplets using microfluidic and EWOD-based systems. In some forms, biopolymers including nucleic acids, peptides, carbohydrates, and lipids are synthesized from step-wise assembly of building blocks based on a user-defined sequence of droplet movements. In some forms, the methods synthesize uniquely addressed nucleic acids of up to 1,000 nucleotides in length. Methods for adding, removing and changing barcodes on biopolymers are also provided. Biopolymers synthesized according to the methods, and libraries and databases thereof are also described. Modified biopolymers, including chemically modified nucleotides and biopolymers conjugated to other molecules are described.

专利号:US-2009270321-A1
优先权日:2008-04-10
标题 :Over-expression of MPS-1 gene or its gene product(s) results in reduction in size of a variety of malignancies
发明人：STACK JR BRENDAN CURRAN; DAI YUEMENG
权利人:STACK JR BRENDAN CURRAN; DAI YUEMENG
摘要:Metallopanstimulin-1 (MPS-1) is a multifunctional ribosomal protein. MPS-1 is a 10 kD zinc finger protein (ZFP) that is present in all tissues and expressed in increased quantities in a wide variety of proliferating tissues and malignancies. The ribosome is a ribonucleoprotein complex of ribosomal RNAs (rRNA) and proteins (r-protein). Conventionally, r-proteins are thought to be responsible for new protein synthesis, but emerging evidence has shown activity exists beyond this. Some extra-ribosomal functions of r-proteins have been observed in close relation to cancer pathology. MPS-1 is over-expressed in the serum and tissue of dozens of malignancies. However, it is unknown whether the enhanced expression of MPS-1 is the cause or result of tumor development and progression. Our preliminary observations show increased MPS-1 decreases paxillin. Recently, paxillin was found to have an important role in regulating both normal and tumor cell proliferation. n Elevation of MPS-1 in HNSCC samples and its structure/function as a ribosomal ZFP have led us to conclude that MPS-1 might be a subject of interest for malignant tumor therapy. Our data reveal that enhanced expression of MPS-1 protein can strongly suppress tumor cell proliferation. MPS-1 and significantly inhibits tumor growth both in vitro and in vivo in 3 distinct malignant cell lines. We have concluded that over-expression of MPS-1 might be used therapeutically in the treatment of some malignancies.

专利号:EP-0635577-B1
优先权日:1993-07-23
标题 :Screen for inhibitors of melanin biosynthesis
发明人：BRINDLE FRANCES HARRIET ELIZAB; FROELIGER EUNICE HARRIET
权利人:BASF AG
摘要:A method for the identification of agents that inhibit melanin biosynthesis involves the incubation of test samples in cultures of a fungus that produces melanin. Observation of altered pigmentation in the culture or culture area containing test sample indicates inhibition of melanin biosynthesis. Preferred cultures for the screen contain a fungus that pigments in the light or the dark such as Cladosporium cucumerinum. Preferred embodiments employ test samples on disks or in wells in solidified cultures and a known melanin synthesis inhibitor as a positive control which is compared to the test sample by simple visual inspection.

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主要参考文献

1: Pillai JR, Wali AF, Shivappa P, Talath S, Attia SM, Nadeem A, Rehman MU. Evaluating the anti-cancer potential and pharmacological in-sights of Physalis angulata Root Extract as a strong candidate for future research. J Genet Eng Biotechnol. 2024 Dec;22(4):100410. doi: 10.1016/j.jgeb.2024.100410. Epub 2024 Aug 22.
2: Cai W, Teng T, Wang X, Li B, Gu X, Zhou Y. Thiolutin Alleviates Cardiotoxic Effects of Doxorubicin by Suppressing NLRP3 Inflammasome in the Mouse Model. Cardiovasc Toxicol. 2024 Dec 11. doi: 10.1007/s12012-024-09947-1. Epub ahead of print. 63(49):e202410799. doi: 10.1002/anie.202410799. Epub 2024 Oct 18. 14(1):40. doi: 10.1007/s13659-024-00460-0.
5: Ri-Wen, Yang YH, Zhang TN, Liu CF, Yang N. Targeting epigenetic and post- translational modifications regulating pyroptosis for the treatment of inflammatory diseases. Pharmacol Res. 2024 May;203:107182. doi: 10.1016/j.phrs.2024.107182. Epub 2024 Apr 12. 115(4):1196-1208. doi: 10.1111/cas.16090. Epub 2024 Jan 30.