2-氯甲基-4h-吡啶并[1,2-a]嘧啶-4-酮 | 16867-35-9

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 中文名称: 2-氯甲基-4h-吡啶并[1,2-a]嘧啶-4-酮
• 中文别名: 2-氯甲基-4H-吡啶并[1,2-A]嘧啶-4-酮
• 英文名称: 2-(chloromethyl)-4H-pyrido[1,2-a]pyrimidin-4-one
• 英文别名: 2-(chloromethyl)pyrido[1,2-a]pyrimidin-4-one
• CAS: 16867-35-9
• 化学式: C₉H₇ClN₂O
• mdl: MFCD03001117
• 分子量: 194.62
• InChiKey: QANDFEYEAYUSKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090
• 储存条件：
  存储条件：2-8°C，密封保存，干燥环境。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2-(Chloromethyl)-4h-pyrido[1,2-a]pyrimidin-4-one
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: 2-(Chloromethyl)-4h-pyrido[1,2-a]pyrimidin-4-one
CAS number: 16867-35-9

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C9H7ClN2O
Molecular weight: 194.6

---

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 chloride.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-氯甲基-4h-吡啶并[1,2-a]嘧啶-4-酮 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 13-Anilino-2-oxo-17-phenyl-12-thia-3,9,16-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),4,6,8,11(15),13,16-heptaene-14-carbonitrile
  参考文献：
  名称：

  Pictet-Spengler 环化合成新型四环噻吩并[3',2':2,3]吡啶并[4,5-d]吡啶并[1,2-a]嘧啶酮

  摘要：

  Synthesis of novel thieno[3',2':2,3]pyrido[4,5-d]pyrido[1,2-a]pyrimidin-5-one derivatives (5) via Pictet-Spengler cyclization is reported. The key intermediate, 2-(3-amino-4-cyano-5-phenylaminothieno-2-yl)-4H-pyrido[1,2-a]pyrimidin-4-one (3), was readily prepared from 2-chloromethy1-4Hpyrido[1,2-a]pyrimidin-4-one (1) with potassium (2,2-dicyano-1-phenylaminoethen-1-yl)thiolate (2) by Thorpe-Ziegler isomerization. Reaction of the intermediate amine with aromatic aldehydes in the presence of p-TsOH gives tetracyclic thienopyridine-fused pyrido[1,2-a]pyrimidines 5 in good yields.

  DOI：

  10.3987/com-17-13734
• 作为产物：
  描述：

  4-氯乙酰乙酸乙酯 在 PPA 作用下， 反应 2.0h， 以99%的产率得到2-氯甲基-4h-吡啶并[1,2-a]嘧啶-4-酮
  参考文献：
  名称：

  Mitotic kinesin inhibitors

  摘要：

  本发明涉及用于治疗细胞增殖性疾病，治疗至少部分由KSP介导的疾病以及抑制KSP的化合物。本发明还涉及包含这种化合物的制药组合物，通过给予这种组合物治疗癌症的方法，以及制备这种化合物的方法。本发明的化合物具有以下结构式：

  公开号：

  US20050228002A1

文献信息

• Substituted pyrimidinyl organophosphorus insecticides
  申请人：Uniroyal Chemical Company, Inc.

  公开号：US04634690A1

  公开（公告）日：1987-01-06

  An organophosphorus compound having the structural formula ##STR1## where R is C.sub.1 -C.sub.4 alkyl; R.sup.1 is hydrogen or methyl; or R and R.sup.1 together are a diradical having the formula --SC(Y).dbd.Z--, where Y is halogen, hydrogen or C.sub.1 -C.sub.2 alkyl; and Z is nitrogen, CH, C(CH.sub.3) or C(C.sub.2 H.sub.5) with the proviso that if Y is hydrogen, Z cannot be CH; R.sup.2 is hydrogen, chlorine or bromine; R.sup.3 is methyl or ethyl; R.sup.4 is methoxy, ethoxy, --SCH.sub.3 or --SC.sub.2 H.sub.5 ; and X is oxygen or sulfur and their hydrochlorides is disclosed. These compounds are useful as insecticides or nematocides. In another aspect of this invention a method of controlling rice planthoppers is provided. In this method an insecticidally effective amount of a compound having the formula given above where R is C.sub.1 -C.sub.4 alkyl or benzyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.3 alkyl; or R and R.sup.1 together are a diradical selected from the group consisting of --CH.dbd.CH--CH.dbd.CH--, --CH.dbd.CCl--CH.dbd.CH--, --CH.dbd.C(CH.sub.3)--CH.dbd.CH-- and --SC(Y).dbd.Z--, where Y is halogen, hydrogen or C.sub.1 -C.sub.2 alkyl; and Z is nitrogen, CH, C(CH.sub.3) or C(C.sub.2 H.sub.5); R.sup.2 is hydrogen or bromine; R.sup.3 is methyl or ethyl; R.sup.4 is methoxy, ethoxy or propylthio, with the proviso that if R.sup.2 is bromine, R.sup.4 is propylthio, and X is oxygen or sulfur is applied to the loci where rice planthoppers reside.

  一种具有结构式##STR1##的有机磷化合物，其中R为C.sub.1 -C.sub.4烷基；R.sup.1为氢或甲基；或者R和R.sup.1一起是具有--SC(Y).dbd.Z--式的双自由基，其中Y为卤素、氢或C.sub.1 -C.sub.2烷基；Z为氮、CH、C(CH.sub.3)或C(C.sub.2 H.sub.5)，但如果Y为氢，则Z不能为CH；R.sup.2为氢、氯或溴；R.sup.3为甲基或乙基；R.sup.4为甲氧基、乙氧基、--SCH.sub.3或--SC.sub.2 H.sub.5；X为氧或硫及其盐酸盐。这些化合物可用作杀虫剂或线虫杀虫剂。在本发明的另一个方面中提供了一种控制稻飞虱的方法。在这种方法中，将具有上述给定结构式的化合物的杀虫有效量施用于稻飞虱栖息地，其中R为C.sub.1 -C.sub.4烷基或苄基；R.sup.1为氢或C.sub.1 -C.sub.3烷基；或者R和R.sup.1一起是从--CH.dbd.CH--CH.dbd.CH--、--CH.dbd.CCl--CH.dbd.CH--、--CH.dbd.C(CH.sub.3)--CH.dbd.CH--和--SC(Y).dbd.Z--组成的双自由基中选择的一种，其中Y为卤素、氢或C.sub.1 -C.sub.2烷基；Z为氮、CH、C(CH.sub.3)或C(C.sub.2 H.sub.5)；R.sup.2为氢或溴；R.sup.3为甲基或乙基；R.sup.4为甲氧基、乙氧基或丙硫基，但如果R.sup.2为溴，则R.sup.4为丙硫基；X为氧或硫。
• [EN] NITROGEN-CONTAINING BICYCLIC HETEROCYCLES FOR USE AS ANTIBACTERIALS<br/>[FR] HETEROCYCLES BICYCLIQUES CONTENANT DE L'AZOTE ET UTILISES COMME PRODUITS ANTIBACTERIENS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2003087098A1

  公开（公告）日：2003-10-23

  Cyclohexane and cyclohexene derivatives and pharmaceutically acceptable derivatives hereof useful in methods of treatment of bacterial infections in mammals, particularly man.

  环己烷和环己烯衍生物及其在哺乳动物，特别是人类细菌感染治疗方法中有用的药用可接受衍生物。
• Pyridopyrimidinone compounds
  申请人：Uniroyal, Inc.

  公开号：US04395551A1

  公开（公告）日：1983-07-26

  A compound of the formula ##STR1## wherein R and R.sup.1 together form a 1,3-butadien-1,4-diyl group optionally substituted with a methyl or chloro group and R.sup.2 is halogen is disclosed. The compound is useful as an intermediate in the synthesis of insecticidal organophosphorus compounds.

  公式为##STR1##的化合物揭示了其中R和R.sup.1共同形成1,3-丁二烯-1,4-二基基团，该基团可以选择性地被甲基或氯代取代，而R.sup.2为卤素。该化合物在合成杀虫有机磷化合物的中间体中是有用的。
• Synthesis and Antiproliferative Activitiy of Novel Diaryl Ureas Possessing a 4<i>H-</i>Pyrido[1,2-<i>a</i>]pyrimidin-4-one Group
  作者：Peng Yao、Xin Zhai、Dong Liu、Bao Hui Qi、Hai Liang Tan、Yong Cai Jin、Ping Gong

  DOI：10.1002/ardp.200900130

  日期：2009.11.19

  We herein disclose a series of novel diaryl urea derivatives possessing a 4H‐pyrido[1,2‐a]pyrimidin‐4‐one group as novel potent anticancer compounds. The structures were confirmed by IR, 1H‐NMR, and MS. All the compounds were screened for their antiprofilerative activity agaist the human breast cancer cell line (MDA‐MB‐231). The pharmacological results indicated that most of the compounds showed moderate

  我们在此公开了一系列具有 4H-吡啶并[1,2-a]嘧啶-4-one基团的新型二芳基脲衍生物作为新型有效抗癌化合物。结构经IR、1H-NMR和MS确证。筛选了所有化合物对人乳腺癌细胞系 (MDA-MB-231) 的抗特征性活性。药理结果表明，大多数化合物表现出中等活性。该系列中最好的是化合物 4c（IC50 = 0.7 μmol/L），其效力是 2005 年批准的索拉非尼（IC50 = 2.5 μmol/L）的 3.6 倍。
• Discovery of 2-((1H-benzo[d]imidazol-1-yl)methyl)-4H-pyrido[1,2-a]pyrimidin-4-ones as novel PKM2 activators
  作者：Chuangxing Guo、Angelica Linton、Mehran Jalaie、Susan Kephart、Martha Ornelas、Mason Pairish、Samantha Greasley、Paul Richardson、Karen Maegley、Michael Hickey、John Li、Xin Wu、Xiaodong Ji、Zhi Xie

  DOI：10.1016/j.bmcl.2013.03.090

  日期：2013.6

  pyruvate kinase is an emerging target for antitumor therapy. In this letter, we describe the discovery of 2-((1H-benzo[d]imidazol-1-yl)methyl)-4H-pyrido[1,2-a]pyrimidin-4-ones as potent and selective PKM2 activators which were found to have a novel binding mode. The original lead identified from high throughput screening was optimized into an efficient series via computer-aided structure-based drug design

  丙酮酸激酶的M2同工型是抗肿瘤治疗的新兴目标。在这封信中，我们描述了发现2-（（1 H-苯并[ d ]咪唑-1-基）甲基）-4 H-吡啶基[1,2- a ]嘧啶-4-酮的发现，这是有力且选择性的PKM2被发现具有新型结合模式的活化剂。通过计算机辅助基于结构的药物设计，将从高通量筛选中鉴定出的原始铅优化为有效系列。该系列中的代表性化合物和文献中描述的活化剂均被用作分子工具来探测PKM2活化对癌细胞的生物学作用。我们的结果表明，单独的PKM2激活不足以改变癌细胞的代谢。