(5,6-二甲基噻吩并[2,3-d]嘧啶-4-磺酰基)-乙酸 | 296262-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 中文名称: (5,6-二甲基噻吩并[2,3-d]嘧啶-4-磺酰基)-乙酸
• 英文名称: 2-((5,6-dimethylthieno[2,3-d]pyrimidin-4-yl)thio)acetic acid
• 英文别名: [(5,6-dimethylthieno[2,3-d]pyrimidin-4-yl)thio]acetic acid；2-(5,6-dimethylthieno[2,3-d]pyrimidin-4-ylthio)acetic acid；(5,6-Dimethyl-thieno[2,3-d]pyrimidin-4-ylsulfanyl)-acetic acid；2-(5,6-dimethylthieno[2,3-d]pyrimidin-4-yl)sulfanylacetic acid
• CAS: 296262-16-3
• 化学式: C₁₀H₁₀N₂O₂S₂
• mdl: MFCD00449576
• 分子量: 254.334
• InChiKey: VSOXJMQZOPRPGI-UHFFFAOYSA-N

物化性质

• 熔点：
  209-210 °C
• 沸点：
  476.0±45.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2934999090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (5,6-Dimethyl-thieno[2,3-d]pyrimidin-4-ylsulfanyl)-acetic 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: (5,6-Dimethyl-thieno[2,3-d]pyrimidin-4-ylsulfanyl)-acetic acid
CAS number: 296262-16-3

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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: C10H10N2O2S2
Molecular weight: 254.3

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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

反应信息

• 作为反应物：
  描述：

  (5,6-二甲基噻吩并[2,3-d]嘧啶-4-磺酰基)-乙酸 在 氨 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 生成 2-((5,6-dimethylthieno[2,3-d]pyrimidin-4-yl)thio)acetamide
  参考文献：
  名称：

  Stimulation of cortical bone formation with thienopyrimidine based inhibitors of Notum Pectinacetylesterase

  摘要：

  A group of small molecule thienopyrimidine inhibitors of Notum Pectinacetylesterase are described. We explored both 2-((5,6-thieno[2,3-d]pyrimidin-4-yl)thio)acetic acids and 2-((6,7-thieno[3,2-d]pyrimidin-4-yl)thio)acetic acids. In both series, highly potent, orally active Notum Pectinacetylesterase inhibitors were identified. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.02.021
• 作为产物：
  描述：

  5,6-二甲基噻吩[2,3-D]嘧啶-4(3H)-酮 在 tetraphosphorus decasulfide 、 水 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.08h， 生成 (5,6-二甲基噻吩并[2,3-d]嘧啶-4-磺酰基)-乙酸
  参考文献：
  名称：

  Synthesis and biological evaluation of substituted (thieno[2,3-d]pyrimidin-4-ylthio)carboxylic acids as inhibitors of human protein kinase CK2

  摘要：

  A novel series of substituted (thieno[2,3-d]pyrimidin-4-ylthio)carboxylic acids has been synthesized and tested in vitro towards human protein kinase CK2. It was revealed that the most active compounds inhibiting CK2 are 3-{[5-(4-methylphenyl)thieno[2,3-d]pyrimidin-4-yl]thio}propanoic acid and 3-{[5-(4-ethoxyphenyl)thieno[2,3-d]pyrimidin-4-yl]thio}propanoic acid (IC50 values are 0.1 mu M and 0.125 mu M, respectively). Structure activity relationships of 28 tested thienopyrimidine derivatives have been studied and binding mode of this chemical class has been predicted. Evaluation of the inhibitors on seven protein kinases revealed considerable selectivity towards CK2. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.025

文献信息

• INHIBITORS OF NOTUM PECTINACETYLESTERASE AND METHODS OF THEIR USE
  申请人：BARBOSA Joseph

  公开号：US20120065200A1

  公开（公告）日：2012-03-15

  Compounds are disclosed for the treatment, management and prevention of diseases and disorders affecting the bone. Particular compounds are potent inhibitors of Notum Pectinacetylesterase, and are of the formula: wherein E, G, Y, Z, R 1 , R 2 , and R 3 are defined herein.

  揭示了用于治疗、管理和预防影响骨骼的疾病和紊乱的化合物。特定的化合物是Notum果胶乙酰酶的强效抑制剂，化学结构如下：其中E、G、Y、Z、R1、R2和R3如本文所定义。
• Scaffold-hopping identifies furano[2,3-d]pyrimidine amides as potent Notum inhibitors
  作者：Benjamin N. Atkinson、David Steadman、William Mahy、Yuguang Zhao、James Sipthorp、Elliott D. Bayle、Fredrik Svensson、George Papageorgiou、Fiona Jeganathan、Sarah Frew、Amy Monaghan、Magda Bictash、E. Yvonne Jones、Paul V. Fish

  DOI：10.1016/j.bmcl.2019.126751

  日期：2020.2

  The carboxylesterase Notum is a key negative regulator of the Wnt signaling pathway by mediating the depalmitoleoylation of Wnt proteins. Our objective was to discover potent small molecule inhibitors of Notum suitable for exploring the regulation of Wnt signaling in the central nervous system. Scaffold-hopping from thienopyrimidine acids 1 and 2, supported by X-ray structure determination, identified 3-methylimidazolin-4-one amides 20-24 as potent inhibitors of Notum with activity across three orthogonal assay formats (biochemical, extra-cellular, occupancy). A preferred example 24 demonstrated good stability in mouse microsomes and plasma, and cell permeability in the MDCK-MDR1 assay albeit with modest P-gp mediated efflux. Pharmacokinetic studies with 24 were performed in vivo in mouse with single oral administration of 24 showing good plasma exposure and reasonable CNS penetration. We propose that 24 is a new chemical tool suitable for cellular studies to explore the fundamental biology of Notum.
• [EN] INHIBITORS OF NOTUM PECTINACETYLESTERASE AND METHODS OF THEIR USE<br/>[FR] INHIBITEURS DE LA NOTUM PECTINE ACÉTYLESTÉRASE ET PROCÉDÉS POUR LEUR UTILISATION
  申请人：LEXICON PHARMACEUTICALS INC

  公开号：WO2012037141A1

  公开（公告）日：2012-03-22

  Compounds are disclosed for the treatment, management and prevention of diseases and disorders affecting the bone. Particular compounds are potent inhibitors of Notum Pectinacetylesterase, and are of the formula: wherein E, G, Y, Z, R1, R2, and R3 are defined herein.
• Synthesis and biological evaluation of substituted (thieno[2,3-d]pyrimidin-4-ylthio)carboxylic acids as inhibitors of human protein kinase CK2
  作者：Andriy G. Golub、Volodymyr G. Bdzhola、Nadiia V. Briukhovetska、Anatoliy O. Balanda、Olexander P. Kukharenko、Igor M. Kotey、Olga V. Ostrynska、Sergiy M. Yarmoluk

  DOI：10.1016/j.ejmech.2010.12.025

  日期：2011.3

  A novel series of substituted (thieno[2,3-d]pyrimidin-4-ylthio)carboxylic acids has been synthesized and tested in vitro towards human protein kinase CK2. It was revealed that the most active compounds inhibiting CK2 are 3-[5-(4-methylphenyl)thieno[2,3-d]pyrimidin-4-yl]thio}propanoic acid and 3-[5-(4-ethoxyphenyl)thieno[2,3-d]pyrimidin-4-yl]thio}propanoic acid (IC50 values are 0.1 mu M and 0.125 mu M, respectively). Structure activity relationships of 28 tested thienopyrimidine derivatives have been studied and binding mode of this chemical class has been predicted. Evaluation of the inhibitors on seven protein kinases revealed considerable selectivity towards CK2. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Stimulation of cortical bone formation with thienopyrimidine based inhibitors of Notum Pectinacetylesterase
  作者：James E. Tarver、Praveen K. Pabba、Joseph Barbosa、Qiang Han、Michael W. Gardyan、Robert Brommage、Andrea Y. Thompson、James M. Schmidt、Alan G.E. Wilson、Wei He、Victoria K. Lombardo、Kenneth G. Carson

  DOI：10.1016/j.bmcl.2016.02.021

  日期：2016.3

  A group of small molecule thienopyrimidine inhibitors of Notum Pectinacetylesterase are described. We explored both 2-((5,6-thieno[2,3-d]pyrimidin-4-yl)thio)acetic acids and 2-((6,7-thieno[3,2-d]pyrimidin-4-yl)thio)acetic acids. In both series, highly potent, orally active Notum Pectinacetylesterase inhibitors were identified. (C) 2016 Elsevier Ltd. All rights reserved.