2-氨基-5-溴噻唑-4-甲酸乙酯 | 61830-21-5

• 物质功能分类: 香精与香料 - 合成香料 - 内酯和含氧杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-氨基-5-溴噻唑-4-甲酸乙酯
• 中文别名: 乙基-2-氨基-5-溴噻唑-4-羧酸乙酯；2-氨基-5-溴-4-噻唑甲酸乙酯；2-氨基-5-溴-4-噻唑羧酸乙酯
• 英文名称: ethyl 2-amino-5-bromothiazole-4-carboxylate
• 英文别名: 2-amino-5-bromthiazol-4-carbonic acid ethyl ester；ethyl 2-amino-5-bromo-1,3-thiazole-4-carboxylate
• CAS: 61830-21-5
• 化学式: C₆H₇BrN₂O₂S
• 分子量: 251.104
• InChiKey: TWGNDRMYYDZGFI-UHFFFAOYSA-N

物化性质

• 熔点：
  115-117 °C
• 沸点：
  357.0±22.0 °C(Predicted)
• 密度：
  1.731±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934100090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 2-amino-5-bromothiazole-4-carboxylate
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: Ethyl 2-amino-5-bromothiazole-4-carboxylate
CAS number: 61830-21-5

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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: C6H7BrN2O2S
Molecular weight: 251.1

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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, hydrogen bromide, 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

反应信息

• 作为反应物：
  描述：

  2-氨基-5-溴噻唑-4-甲酸乙酯 在 磷酸 、 硝酸 、 sodium nitrite 、 potassium iodide 作用下， 以 水 为溶剂， 反应 1.0h， 以69%的产率得到ethyl 5-bromo-2-iodothiazole-4-carboxylate
  参考文献：
  名称：

  基于二噻唑基噻吩并噻吩双酰亚胺的 π 共轭聚合物：改进的合成和作为 P 型半导体的有机光伏应用

  摘要：

  二噻唑基噻吩并噻吩双酰亚胺（TzBI）由于其强缺电子性和高共面性，是一种很有前途的供体-受体 π 共轭聚合物的构建单元。我们之前报道了一个...

  DOI：

  10.1246/bcsj.20200016
• 作为产物：
  描述：

  3-溴丙酮酸乙酯 在 溴 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 13.5h， 生成 2-氨基-5-溴噻唑-4-甲酸乙酯
  参考文献：
  名称：

  噻唑基吡咯烷酮和异吲哚二酮类作为抗惊厥剂的合成，生物学评价和分子对接研究

  摘要：

  摘要合成了一系列新的1-（噻唑-2-基）吡咯烷-2-酮5a – m和2-（噻唑-2-基）异吲哚啉-1,3-二酮6a – n衍生物，并评估了其抗惊厥活性。该活动建立在三种癫痫发作模型中：PTZ，微毒素和MES。通过旋转脚踏试验选择出的化合物具有神经毒性。该系列中活性最高的化合物是1-（4-（萘-2-基）噻唑-2-基）吡咯烷酮-2-酮（5g），PTZ效应剂量（ED 50）值为18.4 mg / kg在小鼠中。中毒剂量（TD 50）为170.2 mg / kg，可提供保护指数（PI = TD 50 / ED 50）的9.2。还进行了计算研究，包括药代动力学特性预测和对接研究。在光谱数据和单晶X射线晶体学的基础上阐明了新合成化合物的结构分配。 图形概要合成了一系列新的基于噻唑的吡咯烷酮5a – m和异吲哚二酮6a – l，并作为抗惊厥药进行了测试。活性最高的化合物是1-（4-（萘-2-基）噻唑-2-基）吡咯烷酮-2-酮（5g），ED

  DOI：

  10.1007/s00044-015-1371-3

文献信息

• [EN] 6,7-DIHYDRO-5H-PYRIDO[2,3-C]PYRIDAZINE DERIVATIVES AND RELATED COMPOUNDS AS BCL-XL PROTEIN INHIBITORS AND PRO-APOPTOTIC AGENTS FOR TREATING CANCER<br/>[FR] DÉRIVÉS DE 6,7-DIHYDRO-5H-PYRIDO[2,3-C]PYRIDAZINE ET COMPOSÉS APPARENTÉS EN TANT QU'INHIBITEURS DE PROTÉINE BCL-XL ET AGENTS PRO-APOPTOTIQUES POUR LE TRAITEMENT DU CANCER
  申请人：SERVIER LAB

  公开号：WO2021018858A1

  公开（公告）日：2021-02-04

  The present invention discloses 6,7-dihydro-5H-pyrido[2,3- c]pyridazine, 1,2,3,4-tetrahydroquinoline, 1H-indole, 3,4- dihydro-2H-1,4-benzoxazine, 1H-pyrrolo[2,3-b]pyridin-1-yl, 7H- pyrrolo[2,3-c]pyridazine, 5H,6H,7H,8H,9H-pyridazino[3,4-b]azepine derivatives and related compounds of formula (I) as Bcl-xL protein inhibitors for use as pro-apoptotic agents for treating cancer, autoimmune diseases or immune system diseases. Formula (I). The description discloses the preparation of exemplary compounds (e.g. pages 113 to 354 examples 1 to 221) as well as pharmacological studies with relevant data (e.g. pages 355 to 367; examples A to E; tables 1 to 5). Exemplary compounds are e.g. 2-6-[(1,3-benzothiazol-2-yl) amino]-1,2,3,4-tetrahydroquinolin-1-yl}-1,3-thiazole-4-carboxylic acid (example 1) or e.g. 3-1-[(adamantan-1-yl)methyl]-5- methyl-1H-pyrazol-4-yl}-6-3-[(1,3-benzothiazol-2-yl)amino]-4- methyl-5H,6H,7H,8H-pyrido[2,3-c]pyridazin-8-yl]pyridine-2-carboxylic acid (example 24).

  本发明公开了作为Bcl-xL蛋白抑制剂用于治疗癌症、自身免疫疾病或免疫系统疾病的促凋亡剂的6,7-二氢-5H-吡啶并[2,3-c]吡啶嗪、1,2,3,4-四氢喹啉、1H-吲哚、3,4-二氢-2H-1,4-苯并噁嗪、1H-吡咯并[2,3-b]吡啶-1-基、7H-吡咯并[2,3-c]吡啶嗪、5H,6H,7H,8H,9H-吡啶并[3,4-b]氮杂环庚烷衍生物和相关化合物的化学式(I)。描述了示例化合物的制备（例如第113至354页的示例1至221）以及具有相关数据的药理学研究（例如第355至367页；示例A至E；表1至5）。示例化合物包括例如2-6-[(1,3-苯并噻唑-2-基)氨基]-1,2,3,4-四氢喹啉-1-基}-1,3-噻唑-4-羧酸（示例1）或例如3-1-[(1-金刚烷-1-基)甲基]-5-甲基-1H-吡唑-4-基}-6-3-[(1,3-苯并噻唑-2-基)氨基]-4-甲基-5H,6H,7H,8H-吡啶并[2,3-c]吡啶-8-基]吡啶-2-羧酸（示例24）。
• The effect of benzenesulfonamide's side chains on their human carbonic anhydrase Ⅰ/Ⅱ inhibitory activities
  作者：Chaofu Yang、Xianyu Sun、Zhan Li、Yunyun Cheng、Yu Lei、Liang Lu、Xuan Liu、Xiaomei Zhuang、Tao Wang、Xinhua He

  DOI：10.1016/j.molstruc.2021.131927

  日期：2022.2

  against carbonic anhydrases (CAs), 12 benzenesulfonamides containing hydrophilic tails and 16 benzenesulfonamides containing hydrophobic tails were designed and synthesized. Benzenesulfonamides with hydrophilic tails including 4b, 4c, and 5b and benzenesulfonamides with hydrophobic tails including 2e, 4b, and 4c are potent carbonic anhydrase Ⅰ/Ⅱ dual inhibitors whose Ki to CA I and CA II were below 10

  苯磺酰胺是众所周知的强效碳酸酐酶抑制剂 (CAI)。它们通常由苯磺酰胺头部和疏水性侧链尾部组成。然而，疏水性侧链尾部导致水溶性差，这是 CAI 开发中的一个主要挑战。在此，为了详细说明具有亲水/疏水尾部的苯磺酰胺是否对碳酸酐酶（CA）有效，设计并合成了 12 种含有亲水尾部的苯磺酰胺和 16 种含有疏水尾部的苯磺酰胺。具有亲水尾部的苯磺酰胺，包括4b、4c和5b，以及具有疏水尾部的苯磺酰胺，包括2e、4b和4c是有效的碳酸酐酶 I/II 双重抑制剂，其 Ki 对 CA I 和 CA II 分别低于 10 nM 和低于 50 nM。然而，4b、4c和5b 的水溶性分别为52、148和 71 mg/100 g 水，远优于具有疏水尾的苯磺酰胺。在缺氧小鼠模型中，与空白对照相比，化合物4c和5b 分别将小鼠的存活率延长了 34.46% 和 28.23%。治疗4C和5B延长生存期比乙酰唑胺治疗好做（16
• 2-Thioethenyl substituted carbapenem derivatives
  申请人：Maruyama Takahisa

  公开号：US20070004700A1

  公开（公告）日：2007-01-04

  [Objective] An objective of the present invention is to provide compounds that are effective against various resistant bacteria which cause current clinical problems, for example, pneumococci including penicillin resistant Streptococcus pneumoneae (PRSP), Haemophilus influenzae including bata-lactamase-nonproducing ampicillin-resistant Haemophilus influenzae (BLNAR), and Moraxella ( Branhamella ) catarrhalis. [Structure] The present invention provides 2-ethenylthio-based carbapenem derivatives represented by the formula (I) or pharmaceutically acceptable salts thereof that are effective, for example, against pneumococci including penicillin resistant Streptococcus pneumoneae (PRSP), Haemophilus influenzae including beta-lactamase-nonproducing ampicillin-resistant Haemophilus influenzae (BLNAR), and Moraxella (Branhamella) catarrhalis:

  本发明的一个目标是提供对抗引起当前临床问题的各种耐药细菌有效的化合物，例如对抗青霉素耐药的肺炎球菌（PRSP）、包括产β-内酰胺酶非产生性氨苄青霉素耐药的流感嗜血杆菌（BLNAR）和喜马拉雅链球菌（布兰氏链球菌）等。本发明提供了以公式（I）表示的基于2-乙烯硫的碳青霉烯衍生物或其药用可接受盐，例如对抗青霉素耐药的肺炎球菌（PRSP）、包括产β-内酰胺酶非产生性氨苄青霉素耐药的流感嗜血杆菌（BLNAR）和喜马拉雅链球菌（布兰氏链球菌）有效。
• Oxazoles and their agricultural compositions
  申请人：Zeneca Limited

  公开号：US05705516A1

  公开（公告）日：1998-01-06

  A compound having the formula R--S(O).sub.n CH.sub.2 CH.sub.2 CH.dbd.CF.sub.2, wherein R is a phenyl group or a heterocyclic group selected from furyl, thienyl, isoxazolyl, isothiazolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-oxadiazolyl, 1,3,4-thidiazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,3,4-triazinyl, and 1,3,5-triazinyl groups, said phenyl or heterocyclic group being optionally substituted by optionally substituted alkyl, optionally substituted alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl, alkoxy, alkenyloxy, alkynyloxy, hydroxyalkyl, alkoxyalkyl, optionally substituted aryl, optionally substituted arylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxy, optionally substituted heteroarylalkoxy, optionally substituted heteroaryloxyalkyl, haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy, haloalkenyloxy, haloalkynyloxy, halogen, hydroxy, cyano, nitro, --NR7R8, --NR7COR8, --NR7CSR8, --NR7SO2R8, --N(SO2R7)(SO2R8), --COR7, --CONR7R8, -alkylCONR7R8, --CR7NR8, --COOR7, --OCOR7, --SR7, --SOR7, --SO2R7, -alkylSR7, -alkylSOR7, -alkylSO2R7, --OSO2R7, --SO2NR7R8, --CSNR7R8, --SiR7R8R9, --OCH2CO2R7, --OCH2CH2CO2R7, --CONR7SO2R8, -alkylCONR7SO2R8, --NHCONR7R8, --NHCSNR7R8, or an adjacent pair of R1, R2, R3, R4, R5 and R6 when taken together form a fused 5- or 6-membered carbocyclic or heterocyclic ring; R7, R8 and R9 are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, alkynyl, optionally substituted aryl or optionally substituted arylalkyl, haloalkyl, haloalkenyl, haloalkynyl, halogen or hydroxy.

  具有化学式R--S(O).sub.n CH.sub.2 CH.sub.2 CH.dbd.CF.sub.2的化合物，其中R是苯基或从呋喃基，噻吩基，异噁唑基，异硫唑基，噁唑基，噻唑基，咪唑基，吡唑基，1,2,4-噁二唑基，1,2,4-硫二唑基，1,3,4-噁二唑基，1,3,4-硫二唑基，四唑基，吡啶基，吡啶嗪基，吡嗪基，1,2,3-三嗪基，1,3,4-三嗪基和1,3,5-三嗪基中选择的杂环基，所述苯基或杂环基可以选择地被可选择地取代的烷基，可选择地取代的烯烃基，炔基，环烷基，烷基环烷基，烷氧基，烯氧基，炔氧基，羟基烷基，烷氧基烷基，可选择地取代的芳基，可选择地取代的芳基烷基，可选择地取代的杂芳基，可选择地取代的杂芳基烷基，可选择地取代的芳氧基，可选择地取代的芳基氧基，可选择地取代的芳氧基烷基，可选择地取代的杂芳氧基，可选择地取代的杂芳基氧基烷基，卤代烷基，卤代烯烃基，卤代炔基，卤代烷氧基，卤代烯氧基，卤代炔氧基，卤素，羟基，氰基，硝基，--NR7R8，--NR7COR8，--NR7CSR8，--NR7SO2R8，--N(SO2R7)(SO2R8)，--COR7，--CONR7R8，-烷基CONR7R8，--CR7NR8，--COOR7，--OCOR7，--SR7，--SOR7，--SO2R7，-烷基SR7，-烷基SOR7，-烷基SO2R7，--OSO2R7，--SO2NR7R8，--CSNR7R8，--SiR7R8R9，--OCH2CO2R7，--OCH2CH2CO2R7，--CONR7SO2R8，-烷基CONR7SO2R8，--NHCONR7R8，--NHCSNR7R8，或R1，R2，R3，R4，R5和R6的相邻对一起形成融合的5-或6-成员碳环或杂环环时；R7，R8和R9分别独立地是氢，可选择地取代的烷基，可选择地取代的烯烃基，炔基，可选择地取代的芳基或可选择地取代的芳基烷基，卤代烷基，卤代烯烃基，卤代炔基，卤素或羟基。
• New FBPase inhibitors for diabetes
  申请人：Gubler Marcel

  公开号：US20070281979A1

  公开（公告）日：2007-12-06

  Compounds of formula as well as pharmaceutically acceptable salts and esters thereof, wherein R 1 to R 3 have the significance given in the application and which can be used in the form of pharmaceutical compositions.

  式的化合物，以及其药学上可接受的盐和酯，其中R1至R3具有申请中给定的含义，并可用于制成药物组合物。