2-(3-氧-3,4-二羟基-2H-1,4-苯并噻嗪-2-基)乙酸乙酯 | 82191-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 中文名称: 2-(3-氧-3,4-二羟基-2H-1,4-苯并噻嗪-2-基)乙酸乙酯
• 英文名称: ethyl (3'-oxo-3',4'-dihydro-2'H-1',4'-benzothiazin-2'-yl)acetate
• 英文别名: ethyl 2-(3-oxo-3,4-dihydro-2H-1,4-benzothiazin-2-yl)acetate；2-Ethoxycarbonylmethyl-3,4-dihydro-3-oxo-2H-benzo-1,4-thiazin；Ethylester der 1-Thio-phenmorpholon-(3)-essigsaeure-(2)；ethyl 2-(3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl)acetate；(3-Oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-yl)-essigsaeure-aethylester；(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-yl)-acetic acid ethyl ester；2H-2-(ethoxycarbonylmethyl)-1,4-benzothiazin-3(4H)-one；ethyl 2-(3-oxo-4H-1,4-benzothiazin-2-yl)acetate
• CAS: 82191-17-1
• 化学式: C₁₂H₁₃NO₃S
• 分子量: 251.306
• InChiKey: RLTFSIFTPSJBLB-UHFFFAOYSA-N

物化性质

• 熔点：
  126 °C
• 沸点：
  419.0±38.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 安全说明：
  S24/25
• 储存条件：
  室温

SDS

Name:	Ethyl 2-(3-oxo-3 4-dihydro-2h-1 4-benzothiazin-2-yl)acetate 97% Material Safety Data Sheet
Synonym:	2,3-Dihydro-2-(ethoxycarbonylmethyl)-4H-benzo-1,4-thiazin-3-on
CAS:	82191-17-1

Section 1 - Chemical Product MSDS Name:Ethyl 2-(3-oxo-3 4-dihydro-2h-1 4-benzothiazin-2-yl)acetate 97% Material Safety Data Sheet
Synonym:2,3-Dihydro-2-(ethoxycarbonylmethyl)-4H-benzo-1,4-thiazin-3-on

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
82191-17-1	Ethyl 2-(3-oxo-3,4-dihydro-2H-1,4-benz	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 82191-17-1: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: grey
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 126 - 128 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H13NO3S
Molecular Weight: 251

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Acid chlorides, strong oxidizing agents, bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 82191-17-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 2-(3-oxo-3,4-dihydro-2H-1,4-benzothiazin-2-yl)acetate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 82191-17-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 82191-17-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 82191-17-1 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-(3-氧-3,4-二羟基-2H-1,4-苯并噻嗪-2-基)乙酸乙酯 在 sodium hydroxide 、 potassium carbonate 、 potassium iodide 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二甲基亚砜 为溶剂， 反应 43.0h， 生成 2-[5-甲基-3-氧代-4-(4,5,7-三氟-1,3-苯并噻唑-2-基)-1,4-苯并噻嗪-2-基]乙酸
  参考文献：
  名称：

  Novel and Potent Aldose Reductase Inhibitors: 4-Benzyl- and 4-(Benzothiazol-2-ylmethyl)-3,4-dihydro-3-oxo-2H-1,4-benzothiazine-2-acetic Acid Derivatives.

  摘要：

  合成了多种1,4-苯并噻唑-2-乙酸衍生物（1、2和3）及其生物等效物（15b、16、18和20b），并在体外评估其抑制猪眼晶状体醇糖还原酶（AR）的能力。在体外表现出强效活性的化合物，也在体内测定其对链脲菌素糖尿病大鼠的红细胞、坐骨神经和晶状体中甜菜糖积累的抑制活性。4-(取代苯并噻唑-2-亚甲基)-1,4-苯并噻唑-2-乙酸衍生物（2和3）比4-(4-溴-2-氟苯)-1,4-苯并噻唑-2-乙酸衍生物（1）显示出更强的AR抑制活性。4-(4,5,7-三氟苯并噻唑-2-亚甲基)-3,4-二氢-3-氧-2H-1,4-苯并噻唑-2-乙酸（2q, SPR-210）不仅在体外表现出强效的AR抑制活性（IC50 9.5×10^-9 M），而且在大鼠坐骨神经（ID50 0.1 mg/kg）和晶状体（ID50 9.8 mg/kg）中显著降低了甜菜糖的积累。通过使用(-)-布克因的互变异构盐方法实现了消旋体SPR-210的光学分解。两种对映体（+）-和(-)-SPR-210的生物活性与消旋体相当。

  DOI：

  10.1248/cpb.42.1264
• 作为产物：
  描述：

  2-氨基苯硫醇 在 硫酸 作用下， 以 乙醚 为溶剂， 反应 12.0h， 生成 2-(3-氧-3,4-二羟基-2H-1,4-苯并噻嗪-2-基)乙酸乙酯
  参考文献：
  名称：

  硫酰氯促进了烷基苄硫唑烷乙酸酯中的宝石-二氯化-脱氯化氢：三色色素颜料骨架的合成

  摘要：

  摘要 从邻氨基苯硫酚和顺丁烯二酸酐开始，以非常好的总收率描述了基本的三色色素骨架的化学和立体选择性全合成。该过程涉及相应的1,4-苯并噻嗪-2-基乙酸酯的合成，然后由它们的硫酰氯诱导的二卤代-脱氢卤代，以及与邻氨基硫酚的第二次缩合作为关键步骤。 从邻氨基苯硫酚和顺丁烯二酸酐开始，以非常好的总收率描述了基本的三色色素骨架的化学和立体选择性全合成。该过程涉及相应的1,4-苯并噻嗪-2-基乙酸酯的合成，然后由它们的硫酰氯诱导的二卤代-脱氢卤代，以及与邻氨基硫酚的第二次缩合作为关键步骤。

  DOI：

  10.1055/s-0034-1378714

文献信息

• Hydroxamic acid derivatives
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：US06713477B1

  公开（公告）日：2004-03-30

  A hydroxamic acid derivative represented by formula (1) or a prodrug thereof, or a pharmaceutically acceptable salt thereof, which has a matrix metalo-proteinase inhibitor.

  由式（1）表示的羟羧酸衍生物或其前药，或其药用可接受的盐，具有基质金属蛋白酶抑制剂。
• 1,4-benzothiazine-2-acetic acid derivatives
  申请人：Sapporo Breweries Limited

  公开号：US05252571A1

  公开（公告）日：1993-10-12

  1,4-Benzothiazine-2-acetic acid derivatives having an excellent aldose reductase inhibitory activity which are useful for the prevention and treatment of diabetic complications, such as diabetic cataract, retinopathy, nephropathy and neuropathy.

  具有优秀醛糖还原酶抑制活性的1,4-苯并噻嗪-2-乙酸衍生物，可用于预防和治疗糖尿病并发症，如糖尿病白内障、视网膜病变、肾病和神经病变。
• Bicyclic compounds and compostions as PDF inhibitors
  申请人：Molteni Valentina

  公开号：US20050197326A1

  公开（公告）日：2005-09-08

  This invention is directed to novel bicyclic compounds, to the uses of these compounds in various medicinal applications, including treating disorders amenable to treatment by peptidyl deformylase inhibitors such as treatment of bacterial infections, and to pharmaceutical compositions comprising these compounds.

  本发明涉及新型双环化合物，以及这些化合物在各种医学应用中的用途，包括治疗适用于肽脱甲基酰基酶抑制剂治疗的疾病，如细菌感染的治疗，并涉及包含这些化合物的制药组合物。
• Bicyclic compounds and compositions as PDF inhibitors
  申请人：IRM LLC

  公开号：US07253164B2

  公开（公告）日：2007-08-07

  This invention is directed to novel bicyclic compounds, to the uses of these compounds in various medicinal applications, including treating disorders amenable to treatment by peptidyl deformylase inhibitors such as treatment of bacterial infections, and to pharmaceutical compositions comprising these compounds.

  本发明涉及新型双环化合物，以及这些化合物在各种医学应用中的用途，包括治疗适用于肽变形酶抑制剂治疗的疾病，例如治疗细菌感染，并涉及包含这些化合物的制药组合物。
• BICYCLIC COMPOUNDS AND COMPOSITIONS AS PDF INHIBITORS
  申请人：Molteni Valentina

  公开号：US20070259852A1

  公开（公告）日：2007-11-08

  This invention is directed to novel bicyclic compounds, to the uses of these compounds in various medicinal applications, including treating disorders amenable to treatment by peptidyl deformylase inhibitors such as treatment of bacterial infections, and to pharmaceutical compositions comprising these compounds.

  本发明涉及新型双环化合物、这些化合物在各种药物应用中的用途，包括治疗适用于肽形变酶抑制剂治疗的疾病，例如治疗细菌感染，并涉及包含这些化合物的制药组合物。