猩红酸 | 134-47-4

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸的卤化、磺化、硝化或亚硝化衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 猩红酸
• 中文别名: 6,6'-(1,3-亚脲基)双(1,1'-萘酚)-3,3'-磺酸；7,7-(羰基二亚氨基)二(4-羟基-2-萘磺酸)；6,6"-(1,3-亚脲基)双(1,1"-萘酚)-3,3"-磺酸
• 英文名称: AMI-1
• 英文别名: 7,7'-(carbonylbis(azanediyl))bis(4-hydroxynaphthalene-2-sulfonic acid)；carbonyl J；arginine methyltransferase inhibitor 1；NSC 45174；4,4'-dihydroxy-7,7'-ureylene-bis-naphthalene-2-sulfonic acid；4,4'-Dihydroxy-7,7'-ureylen-bis-naphthalin-2-sulfonsaeure；J Acid urea；4-hydroxy-7-[(5-hydroxy-7-sulfonaphthalen-2-yl)carbamoylamino]naphthalene-2-sulfonic acid
• CAS: 134-47-4
• 化学式: C₂₁H₁₆N₂O₉S₂
• mdl: MFCD00035715
• 分子量: 504.498
• InChiKey: PCGISRHGYLRXSR-UHFFFAOYSA-N

物化性质

• 密度：
  1.798±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：83.33 mg/mL（165.18 mM）

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  207
• 氢给体数：
  6
• 氢受体数：
  9

安全信息

• WGK Germany：
  3
• 海关编码：
  2922210000
• 安全说明：
  S22,S24/25
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6,6’-Ureylene-bis(1-naphthol-3-sulfonic acid)
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 6,6’-Ureylene-bis(1-naphthol-3-sulfonic acid)
CAS number: 134-47-4

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C21H16N2O9S2
Molecular weight: 504.5

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

AMI-1 free acid 是一种有效的细胞渗透性可逆的蛋白精氨酸 N-甲基转移酶 (PRMTs) 抑制剂。其对人 PRMT1 和酵母 HMT1p 的 IC50 值分别为 8.8 μM 和 3.0 μM。AMI-1 free acid 是通过阻断肽-底物结合来抑制 PRMTs 的。

靶点

Target	Value
HMT
human PRMT1
yeast HMT1p (Cell-free assay)	3.0 μM

体外研究

AMI-1 free acid 可以抑制所有五种重组活性 PRMTs（PRMT1、-3、-4 和 -6 以及 HMT1p）的体内甲基化反应。它不仅能够抑制 I 类 PRMTs（PRMT1、3、4 和 6），还能够抑制 II 类 PRMT5。在体外，AMI-1 free acid 特异性地抑制精氨酸而不抑制赖氨酸的甲基转移酶活性，并且不竞争 AdoMet 结合位点。此外，它还能抑制 GFP-Npl3 和细胞蛋白的甲基化。0.6 至 2.4 毫摩尔浓度范围内（48-96 小时）AMI-1 free acid 可以时间依赖性和剂量依赖性地抑制 S180 和 U2OS 细胞的存活率。1.2 至 2.4 毫摩尔浓度范围内的 AMI-1 free acid 在 48-72 小时内通过诱导细胞凋亡减少 S180 细胞的存活率。

实验类型
细胞系	S180 细胞, U2OS 细胞	浓度	0.6 mM, 1.2 mM, 2.4 mM
培养时间	48 小时, 72 小时, 96 小时	结果	抑制细胞存活率

实验类型
细胞系	S180 细胞	浓度	1.2 mM, 2.4 mM
培养时间	48 小时, 72 小时	结果	诱导细胞凋亡增加

体内研究

在肿瘤内每天注射 0.5 毫克 AMI-1 free acid，连续 7 天后可抑制 S180 的存活率。它还下调了肿瘤异种移植模型中的 PRMT5 表达，并降低了 H4R3me2s 和 H3R8me2s 的水平。

实验动物	6-7 周龄雄性昆明小鼠 (18-22 g)，携带有 S180 细胞异种移植
剂量	0.5 mg
给药方式	肿瘤内，每天，7 天
结果	减少了肿瘤重量

用途

AMI-1 free acid 是一种偶氮染料中间体，用于制造直接橙 S 和直接耐酸大红 4BS 等。

反应信息

• 作为反应物：
  描述：

  猩红酸 、 (2E)-3-(4-氨基苯基)-2-丙烯酸 在 硫酸 、 sodium nitrite 、 sodium carbonate 作用下， 生成 (E)-3-[4-[(E)-[1-hydroxy-6-[[5-hydroxy-6-[(E)-[4-[(E)-3-hydroxy-3-oxo-prop-1-enyl]phenyl]azo]-7-sulfo-2-naphthyl]carbamoylamino]-3-sulfo-2-naphthyl]azo]phenyl]prop-2-enoic acid
  参考文献：
  名称：

  羰基J衍生物：一类新的HIV-1整合酶抑制剂。

  摘要：

  病毒复制和致病性需要整合HIV-1基因组的DNA拷贝，而这种高度特异性的分子过程是由病毒编码的整合酶介导的。整合的需要，加上哺乳动物细胞缺乏已知的类似过程，使得整合成为HIV-1复制的治疗性抑制剂的诱人靶标。尽管有许多关于HIV-1 IN抑制剂的报道，但尚未出现用于治疗HIV-1感染的此类化合物。因此，需要新型的整合酶抑制剂。我们已经结合分子建模和组合化学来识别和开发新型的HIV-1整合酶抑制剂，即羰基J [N，N'-双（2-（5-羟基-7-萘磺酸）脲]衍生物。这类新化合物包括许多具有亚微摩尔IC（50）值的化合物，可在体外抑制纯化的HIV-1整合酶。在本文中，我们描述了对于羰基J衍生物内的整合酶抑制和细胞毒性很重要的化学特征。版权所有2000学术出版社。

  DOI：

  10.1006/bioo.2000.1166
• 作为产物：
  描述：

  三光气 、 7-氨基-4-羟基-2-萘磺酸 在 sodium hydroxide 作用下， 反应 6.0h， 以90%的产率得到猩红酸
  参考文献：
  名称：

  Small Molecule Inhibitors of Histone Arginine Methyltransferases:  Homology Modeling, Molecular Docking, Binding Mode Analysis, and Biological Evaluations

  摘要：

  The screening of the inhibition capabilities of dye-like small molecules from a focused library against both human PRMT1 and Aspergillus nidulans RmtA is reported as well as molecular modeling studies (homology modeling, molecular docking, and 3-D QSAR) of the catalytic domain of the PRMT1 fungal homologue RmtA. The good correlation between computational and biological results makes RmtA a reliable tool for screening arginine methyltransferase inhibitors. In addition, the binding mode analyses of tested derivatives reveal the crucial role of two regions, the pocket formed by Ile12, His13, Met16, and Thr49 and the SAM cisteinic binding site subsite. These regions should be taken into account in the design of novel PRMT inhibitors.

  DOI：

  10.1021/jm061213n

文献信息

• Azo dyestuff intermediate nitro- or aminobenzenes ring-substituted by a
  申请人：Sterling Drug Inc.

  公开号：US04146558A1

  公开（公告）日：1979-03-27

  Water-soluble cationic dyestuffs of the formulae ##STR1## WHEREIN R.sup.0 is hydrogen, lower-alkyl or hydroxy-lower-alkyl; R.sup.1 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R.sup.2 is lower-alkyl, lower-alkenyl, hydroxy-lower-alkyl or -(lower-alkylene)-NR.sup.0 Y or R.sup.1 and R.sup.2 together with the nitrogen atom, are pyrrolidino, piperidino or 4-lower-alkanoyl piperazino; Y is hydrogen or ##STR2## wherein R is hydrogen, lower-alkyl, lower-alkenyl, phenyl or phenyl-lower-alkyl; A is a member selected from the group consisting of an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge. K is a small integer whose value is dependent on the nature of A such that it has a range from one to two; R.sup.8 is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R.sup.9 is lower-alkyl, hydroxy-lower-alkyl or NH.sub.2 ; R.sup.10 is lower-alkyl or lower-alkenyl; A.sup.1 is an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge; G is a small integer whose value is dependent on the nature of A.sup.1 such that it has a range from one to two; R.sup.8 ' is lower-alkyl; R.sup.9 ' is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl; R.sup.10 ' is lower-alkyl, lower-alkenyl or hydroxy-lower-alkyl or R.sup.9 ' and R.sup.10 ' together with the nitrogen atom are morpholino; A.sup.2 is an aromatic azo dyestuff residue attached to the quaternary ammonium nitrogen atom through a lower-alkylene bridge; h is a small integer whose value is dependent on the nature of A.sup.2 such that it has a range from one to two; and An is an anion are particularly useful for coloring natural fibers, synthetic fiber-forming materials and cellulosic materials. These dyes dye cotton and paper various shades of stable yellows, reds and oranges. The dyeing from these dyes on paper are less prone to bleed and have a high degree of color discharge when bleached with hypochlorite or chlorine bleaches.

  水溶性阳离子染料的化学式为##STR1## 其中R.sup.0为氢、较低烷基或羟基较低烷基；R.sup.1为较低烷基、较低烯烃基或羟基较低烷基；R.sup.2为较低烷基、较低烯烃基、羟基较低烷基或-(较低烷基)-NR.sup.0 Y或R.sup.1和R.sup.2与氮原子一起，为吡咯烷基、哌啶基或4-较低酰基哌嗪基；Y为氢或##STR2## 其中R为氢、较低烷基、较低烯烃基、苯基或苯基较低烷基；A为从芳香偶氮染料残基中选择的一种，通过较低烷基桥连接到季铵氮原子。K是一个小整数，其值取决于A的性质，范围为一到二；R.sup.8为较低烷基、较低烯烃基或羟基较低烷基；R.sup.9为较低烷基、羟基较低烷基或NH.sub.2；R.sup.10为较低烷基或较低烯烃基；A.sup.1为从芳香偶氮染料残基中选择的一种，通过较低烷基桥连接到季铵氮原子；G是一个小整数，其值取决于A.sup.1的性质，范围为一到二；R.sup.8 '为较低烷基；R.sup.9 '为较低烷基、较低烯烃基或羟基较低烷基；R.sup.10 '为较低烷基、较低烯烃基或羟基较低烷基或R.sup.9 '和R.sup.10 '与氮原子一起为吗啉基；A.sup.2为从芳香偶氮染料残基中选择的一种，通过较低烷基桥连接到季铵氮原子；h是一个小整数，其值取决于A.sup.2的性质，范围为一到二；An为阴离子，特别适用于染色天然纤维、合成纤维形成材料和纤维素材料。这些染料可使棉花和纸张呈现各种稳定的黄色、红色和橙色。这些染料在纸张上的染色不易渗出，漂白时与次氯酸盐或氯漂白剂一起具有高度的色彩释放度。
• Process for the preparation of storage-stable dye dispersions
  申请人：Bayer Corporation

  公开号：EP0747450A2

  公开（公告）日：1996-12-11

  This invention relates to a process for the preparation of storage-stable dye dispersions of alkali metal salts of anionic azo direct dyes by (a) preparing an aqueous slurry of an alkali metal salt of an azo direct dye, said salt having a solubility in water at 25°C of about 0.1 to about 15% by weight, by azo coupling one or more aromatic diazonium salts with one or more couplers while maintaining a pH of at least about 5 by adding a basic alkali metal compound in the absence of a nitrogen-containing base; (b) optionally, stirring the aqueous slurry at a temperature of about 5°C to about 100°C for up to about six hours; (c) optionally, cooling the aqueous slurry to a temperature of about 5°C to about 40°C; and (d) adding to the aqueous slurry a viscosity enhancing agent in an amount sufficient to obtain a viscosity of about 500 to about 5000 centipoise and 0 to about 10% by weight, based on the total weight of the dye dispersion, of a humectant.

  本发明涉及一种通过以下方法制备阴离子偶氮直接染料的碱金属盐的贮存稳定染料分散体的工艺 (a) 制备偶氮直接染料的碱金属盐的水性浆料，所述盐在 25°C 水中的溶解度约为 0.1%至约 15%（按重量计），制备方法是将一种或多种芳香族重氮盐与一种或多种偶联剂进行偶氮偶联，同时在不含含氮碱的情况下加入碱性碱金属化合物，以维持至少约 5 的 pH 值； (b) 可选地，在约 5°C 至约 100°C 的温度下搅拌水性浆料达约 6 小时； (c) 可选地将水性浆液冷却至约 5°C 至约 40°C 的温度；以及 (d) 向水性淤浆中加入一种增粘剂，其用量足以使粘度达到约 500 至约 5000 厘泊，并加入 0 至约 10%（按染料分散液总重量计）的保湿剂。
• Therapeutic agents and methods
  申请人：Pop Test Oncology LLC

  公开号：US11040037B2

  公开（公告）日：2021-06-22

  The invention provides glucocorticoid receptor antagonists for treatment of infection, neoplasia, and fatty liver disease.

  本发明提供了用于治疗感染、肿瘤和脂肪肝的糖皮质激素受体拮抗剂。
• Image making medium
  申请人：——

  公开号：US20030035917A1

  公开（公告）日：2003-02-20

  The invention relates to an image support medium for creation of an aesthetic image that is an work or object for display. This support medium includes a polymer in an amount sufficient to enable the image to have at least one aesthetic element. In different embodiments, the image support medium is an image support stabilizer, the polymer is a synthetic absorbent or conductive polymer, or the polymer is a transparent or synthetic translucent polymer and a property of this transparent or translucent polymer is enhanced to facilitate the creation or preservation of the image by at least one stabilizer. The invention also relates to a method for preparing this image support medium. The method includes forming a reaction mixture comprising a monomer in an amount sufficient to provide or enable the image to have an aesthetic element, and processing the reaction mixture into a 2- or 3-dimensional shape.

  本发明涉及一种图像支持介质，用于创建作为作品或展示对象的美学图像。这种支撑介质包括一种聚合物，其用量足以使图像具有至少一种审美元素。在不同的实施例中，图像支持介质是一种图像支持稳定剂，聚合物是一种合成的吸收性或导电性聚合物，或者聚合物是一种透明或合成的半透明聚合物，并且这种透明或半透明聚合物的特性被至少一种稳定剂增强，以促进图像的创建或保存。本发明还涉及一种制备这种图像支持介质的方法。该方法包括形成由单体组成的反应混合物，其用量足以提供或使图像具有美学元素，并将反应混合物加工成 2 维或 3 维形状。
• Bucherer; Wahl, Journal fur praktische Chemie (Leipzig 1954), 1921, vol. <2> 103, p. 135,136, 151, 153
  作者：Bucherer、Wahl

  DOI：——

  日期：——