6-甲基咪唑并[2,1-B][1,3]噻唑-5-羧肼 | 161563-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并噻唑类
• 中文名称: 6-甲基咪唑并[2,1-B][1,3]噻唑-5-羧肼
• 中文别名: 6-甲基嘧啶-[2,1-B][1,3]噻唑-5-碳酰肼；6-甲基咪唑并[2,1-B![1,3!噻唑-5-羧肼；6-甲基咪唑并[2,1-b]噻唑-5-碳酰肼
• 英文名称: 6-methylimidazo[2,1-b]thiazole-5-carbohydrazide
• 英文别名: 6-methylimidazo<2,1-b>thiazole-5-carbohydrazide；6-Methylimidazo[2,1-b][1,3]thiazole-5-carbohydrazide
• CAS: 161563-79-7
• 化学式: C₇H₈N₄OS
• mdl: MFCD03086213
• 分子量: 196.233
• InChiKey: LPBZKHDAKWWKDV-UHFFFAOYSA-N

物化性质

• 熔点：
  183-184°

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2934100090
• 危险类别：
  IRRITANT
• 安全说明：
  S26,S37/39

SDS

Name:	6-Methylimidazo[2 1-b][1 3]thiazole-5-carbohydrazide 97% Material Safety Data Sheet
Synonym:
CAS:	161563-79-7

Section 1 - Chemical Product MSDS Name:6-Methylimidazo[2 1-b][1 3]thiazole-5-carbohydrazide 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
161563-79-7	6-Methylimidazo[2,1-b][1,3]thiazole-5-	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes 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. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 161563-79-7: 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: off-white
Odor: characteristic odor
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 178 - 180 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: C7H8N4OS
Molecular Weight: 196.23

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
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# 161563-79-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
6-Methylimidazo[2,1-b][1,3]thiazole-5-carbohydrazide - 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 161563-79-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 161563-79-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 161563-79-7 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：

  6-甲基咪唑并[2,1-B][1,3]噻唑-5-羧肼 在 盐酸 、 肼 、 sodium nitrite 作用下， 反应 11.0h， 生成 N-(6-methylimidazo[2,1-b][1,3]thiazol-5-yl)hydrazinecarboxamide
  参考文献：
  名称：

  融合杂环：一些新型咪唑噻唑的合成

  摘要：

  研究了带有咪唑 [2, 1-b] [1,3] 噻唑环系统的醛腙或缩氨基脲与巯基链烷酸的反应。使用利福平作为标准，评价由此获得的化合物对结核分枝杆菌H37RV的抗分枝杆菌活性。由于耐多药结核病在临床实践中的兴起，结核病的治疗仍然是主要问题之一。多年来，异烟酸酰肼（异烟肼）一直被用作治疗疾病的主要药物。取代基和生物等排置换对其抗结核活性的影响仍在研究中 (1)。这促使我们合成 6-methylimidazo [2, l-£>] [1, 3] thiazole-5-carbohydrazide 2，异烟肼的结构类似物，及其迄今为止未报道的衍生物，以筛选其抗结核特性。氩气：a，QH5；b,C,;H4F(4); C,QH4C1(4); d、QH4Br(4)；e, QH4CH3 (4) ; f ,QH4OCH3(4) ; g,QH4NO2(2) 6-Methylimidazo[2,1-b][l,3]t

  DOI：

  10.1515/hc.2002.8.5.433
• 作为产物：
  描述：

  6-甲基咪唑[2,1-B]噻唑-5-羧酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以89%的产率得到6-甲基咪唑并[2,1-B][1,3]噻唑-5-羧肼
  参考文献：
  名称：

  咪唑并[2,1- b ]噻唑和苯并[ d ]咪唑并[2,1- b ]噻唑衍生物作为结核分枝杆菌泛酸合成酶抑制剂的设计，合成及生物学评价

  摘要：

  在本研究中，我们从较早报道的基于咪唑[1,2- a ]吡啶的结核分枝杆菌（MTB）中设计了咪唑并[2,1- b ]噻唑和苯并[ d ]咪唑并[2,1- b ]噻唑衍生物泛酸合成酶（PS）抑制剂。我们合成了30种化合物，并对其进行了MTB PS抑制研究，针对复制性和非复制性MTB的体外抗TB活性，使用分枝杆菌感染斑马鱼的体内活性以及对RAW 264.7细胞系的细胞毒性进行了评估。其中化合物2-甲基-N '-（4-苯氧基苯甲酰基）苯并[ d ]咪唑并[ 2,1- b ]噻唑-3-碳酰肼（5bc）表现为对MTB PS有活性的有效化合物，IC 50为0.53± 0.13μM，MIC为3.53μM，对营养缺乏的MTB降低2.1 log，在50μM时具有33％的细胞毒性。它还显示，斑马鱼中10.00 mg / kg的海螯虾的负载降低了1.5 log 。

  DOI：

  10.1016/j.bmc.2016.01.059

文献信息

• Transformations of methyl<i>L</i>-(-)-thiazolidine-4-carboxylate, 2-amino-2-thiazoline and 2-aminothiazole into thiazoloazines and azolothiazoles
  作者：Mateja Malešíč、Aleš Krbačič、Branko Stanovnik

  DOI：10.1002/jhet.5570340109

  日期：1997.1

  In the search for potential immunomodulators methyl L-(—)-thiazolidine-4-carboxylate (2), 2-amino-2-thiazoline (12), and 2-aminothiazole (19) were transformed into derivatives of various bicyclic systems. Thus, from compound 2 derivatives of perhydrothiazolo[3,4-a]pyrazine 4 and 5, perhydrothiazolo[4,3-c]-[1,4]oxazine 7, and perhydroimidazo[1,5-c]thiazole 9a,b, from compound 12 derivatives of 2,3-dihydro-thiazolo[2

  在寻找潜在的免疫调节剂时，将L -（-）-噻唑烷-4-羧酸甲酯（2），2-氨基-2-噻唑啉（12）和2-氨基噻唑（19）转化为各种双环系统的衍生物。因此，由过氢噻唑并[3，4- a ]吡嗪4和5的化合物2衍生物，全氢噻唑并[4，3- c ]-[1，4]恶嗪7和全氢咪唑并[1，5- c ]噻唑9a，b形成。由2,3-二氢噻唑并[2,3- b ]嘧啶13a，b的化合物12衍生物和咪唑并[2,1- b ]噻唑的化合物19衍生物制备21、22、24和25 。6-（对氨基磺酰基苯基）-7-氧杂氢咪唑[1,5- c发现]噻唑-5-硫酮（9a）具有免疫修复活性。
• Synthesis and antimycobacterial activity of new imidazo[2,1-b]thiazole derivatives
  作者：Z Cesur、H Güner、G Ötük

  DOI：10.1016/0223-5234(94)90199-6

  日期：1994.1
• Ur, Fuesun; Cesur, Nesrin; Birteksoez, Seher, Arzneimittel-Forschung/Drug Research, 2004, vol. 54, # 2, p. 125 - 129
  作者：Ur, Fuesun、Cesur, Nesrin、Birteksoez, Seher、Oetuek, Guelten

  DOI：——

  日期：——
• Design, Synthesis and Biological Assessment of N′-(2-Oxoindolin-3-ylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazides as Potential Anti-Proliferative Agents toward MCF-7 Breast Cancer
  作者：Najla A. Alshaye、Mohamed K. Elgohary、Mahmoud S. Elkotamy、Hatem A. Abdel-Aziz

  DOI：10.3390/ph17020216

  日期：——

  Breast cancer is a serious threat to the health and lives of women. Two novel series of N′-(2-oxoindolin-3-ylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazides and 1-(aryl)-3-(6-methylimidazo[2,1-b]thiazol-5-yl)ureas were designed, synthesized and investigated for their anticancer efficacy against the MCF-7 breast cell line. Three compounds of the first series showed potent activity toward MCF-7 with IC50 in the range 8.38–11.67 µM, respectively, as compared to Sorafenib (IC50 = 7.55 µM). N′-(1-butyl-2-oxoindolin-3-ylidene)-6-methylimidazo[2,1-b]thiazole-5-carbohydrazide inhibited VEGFR-2 with IC50 = 0.33 µM when compared with Sorafenib (IC50 = 0.09 µM). Furthermore, this compound was introduced to PCR assessment, where it increased Bax, caspase 8, caspase 9 and cytochrome C levels by 4.337-, 2.727-, 4.947- and 2.420-fold, respectively, while it decreased levels of Bcl-2, as the anti-apoptotic gene, by 0.359-fold when compared to the untreated control MCF-7. This compound was also arrested in the G2/M phase by 27.07%, compared with 11.31% for the control MCF-7. Furthermore, it induced early and late apoptosis in MCF-7. In addition, a molecular docking study in the VEGFR-2 active site was performed to assess the binding profile for the most active compounds. Moreover, ADME parameters of the targeted compounds were also evaluated.